Tom ntej: 4,6-Dichloro-5-pyrimidinecarbaldehyde CAS 5305-40-8

4,6-Dichloro-5-pyrimidinecarbaldehydeyog ib qho tseem ceeb kws tshuaj thiab tshuaj tua kab nruab nrab nrog cov mis molecular C5H2Cl2N2O. Nws cov yam ntxwv muaj xws li ob chlorine atoms hloov ntawm 4th thiab 6th txoj haujlwm ntawm lub nplhaib pyrimidine, thiab ib pawg formyl (-CHO) txuas ntawm 5 txoj haujlwm. Qhov kev sib xyaw no feem ntau tshwm sim ua dawb rau tawm -dawb crystalline hmoov. Nws cov reactivity siab feem ntau yog los ntawm ob pawg tseem ceeb ua haujlwm: ob lub chlorine atoms ntawm lub nplhaib pyrimidine nthuav tawm cov khoom zoo heev, ua rau lawv muaj kev cuam tshuam rau nucleophilic hloov pauv; pawg formyl, lub sijhawm no, tuaj yeem koom nrog ntau yam kev hloov pauv xws li condensation thiab redox cov tshuaj tiv thaiv, thiab feem ntau siv rau hauv kev tsim kho ntawm heterocyclic compounds. Cov khoom no ua rau nws yog ib qho tseem ceeb hauv cov tshuaj chemistry, tshwj xeeb tshaj yog nyob rau hauv cov synthesis ntawm bioactive molecules xws li anticancer thiab antiviral agents, ua ib tug tseem ceeb lub tsev thaiv rau kev npaj ntawm complex functional molecules. Vim nws cov khoom ua kom khaus khaus, yuav tsum muaj kev tiv thaiv kom zoo thaum lub sij hawm ua haujlwm hauv chav kuaj, thiab nws yuav tsum tau muab cia rau hauv qis - kub, lub teeb - tiv thaiv tej yam kev mob kom ruaj ntseg.

Lub discovery ntawm4,6-Dichloro-5-pyrimidinecarbaldehydetuaj yeem taug qab rov qab mus rau xyoo 1960s thaum ntxov, thaum cov kws tshawb fawb tau nyiam tshawb nrhiav cov tshuaj nrog tshuaj tiv thaiv kab mob. Thaum lub sijhawm tshawb nrhiav, cov kws tshawb fawb tau tshawb pom ntau cov tshuaj tiv thaiv kab mob, hu ua tshuaj tiv thaiv kab mob.
Hauv kev tshawb nrhiav ntau cov tshuaj tiv thaiv kab mob, cov kws tshawb fawb pom 4,6-dichloro-5-pyrimidine formaldehyde. Cov tshuaj no muaj cov tshuaj tiv thaiv kab mob siab heev, yog li nws raug suav hais tias yog tshuaj tiv thaiv kab mob npaws.
Raws li kev tshawb fawb tob zuj zus, cov kws tshawb fawb tau tshawb pom tias cov txheej txheem ntawm kev ua ntawm 4,6-dichloro-5-pyrimidine formaldehyde hauv lub cev txawv ntawm lwm cov tshuaj tiv thaiv kab mob. Nws ua haujlwm los ntawm kev cuam tshuam nrog nucleic acid metabolism ntawm cov kab mob malaria, tsis yog cuam tshuam ncaj qha rau lawv cov DNA. Qhov kev tshawb pom no ua rau 4,6-dichloro-5-pyrimidine formaldehyde yog ib qho ntawm cov qauv tseem ceeb rau kev kawm txog kev ua haujlwm ntawm cov tshuaj tiv thaiv kab mob.

Hauv kev tshawb fawb ntawm cov tshuaj tiv thaiv kab mob, 4,6-dichloro-5-pyrimidine formaldehyde tau dhau los ua qhov pib ntawm ntau yam tshuaj tshiab. Nws muab cov kws tshawb fawb nrog lub hauv paus tsim thiab pab lawv tsim cov tshuaj tiv thaiv kab mob ntau dua nrog kev ua haujlwm siab dua thiab txo qis toxicity. Cov tshuaj no muaj xws li naphthenic acid amine compounds, amino pyrimidine compounds, thiab amino sulfonyl pyrimidine compounds.
Hauv cov ntsiab lus, kev tshawb pom ntawm 4,6-dichloro-5-pyrimidine formaldehyde tau ua haujlwm tseem ceeb rau kev tshawb fawb ntawm cov tshuaj tiv thaiv kab mob.

4,6-Dichloro-5-pyrimidinecarbaldehydeyog ib yam khoom uas muaj ntau yam siv hauv chav kuaj. Yog li ntawd, nws txoj kev synthesis tau dhau los ua ib qho kev taw qhia uas cov kws tshawb fawb tau tshawb nrhiav tas li. Ob txoj kev siv feem ntau hauv Shaanxi Chupeng Chemical Laboratory yog raws li hauv qab no:

Cov kauj ruam synthesis ntawm Txoj Kev 1:

Kauj Ruam 1: Dissolve 4,6-dihydroxypyrimidine hauv qhov tsim nyog ntawm sodium hydroxide tov kom tau txais sodium ntsev tov ntawm 4,6-dihydroxypyrimidine. Tom qab ntawd, chloroform thiab sulfoxide chloride tau ntxiv rau hauv cov tshuaj, rhuab mus rau lub xeev reflux, thiab reacted rau ib lub sij hawm ua ntej txias rau chav tsev kub.

Kauj Ruam 2: Acidify cov tshuaj tiv thaiv nrog tus nqi tsim nyog ntawm dilute hydrochloric acid los hloov cov sodium ntsev ntawm 4,6-dihydroxypyrimidine rau hauv 4,6-dichloropyrimidine.

Kauj Ruam 3: Ntxiv cov dej ammonia kom tsim nyog rau cov tshuaj saum toj no kom nws alkaline, ua kom sov rau lub xeev reflux, hnov ​​​​mob rau qee lub sijhawm, thiab tom qab ntawd txias rau chav tsev kub. Nyob rau ntawm lub sijhawm no, peb tuaj yeem soj ntsuam qhov tsim ntawm ntau qhov dawb precipitate hauv cov tshuaj, uas yog 4,6-dichloro-5-pyrimidine formaldehyde. Tom qab lim, ntxuav, thiab ziab cov khib nyiab, cov khoom xav tau tuaj yeem tau.

Cov hauv qab no yog cov tshuaj sib npaug thaum lub sij hawm ua cov txheej txheem synthesis:

(1) 4,6-Dihydroxypyrimidine reacts nrog sodium hydroxide los ua sodium ntsev ntawm 4,6-Dihydroxypyrimidine:

C₄H₄N₂O₂+2NaOH → C₄H₄N₂O₂Na₂+H₂O

(2) Ntxiv chloroform thiab sulfoxide chloride rau cov tshuaj tiv thaiv:

C₄H₄N₂O₂Na₂+ CWJ₃+ClSOCl → C₄H₃Cl₂N_1O+NaCl+NaClO1S+CH₃Cl

(3) Acidify cov tshuaj tiv thaiv nrog dilute hydrochloric acid:

C₄H₃Cl₂N_1O+2HCl → C₄H₃Cl₂N_1O+ NaCl

(4) Ntxiv dej ammonia los ua cov tshuaj alkaline:

C₄H₃Cl₂N_1O+3NH₃ · H₂O → C₅H₃Cl₂N_1O+3NH₄Cl + H₃O⁺

Ntawm lawv, dej ammonia tuaj yeem hnov ​​​​mob nrog sulfoxide chloride los tsim cov tshuaj ammonium chloride thiab dej, thaum cov tshuaj ammonium chloride tsim los kuj tuaj yeem hnov ​​​​mob nrog sodium hydroxide los tsim ammonium hydroxide thiab sodium chloride. Yog li ntawd, cov khoom ntawm ammonium chloride thiab ammonium hydroxide tsis tau teev nyob rau hauv cov tshuaj sib npaug saum toj no. Tsis tas li ntawd, qee qhov los ntawm - cov khoom xws li polychlorinated pyrimidines tuaj yeem tsim tau thaum lub sijhawm cov tshuaj tiv thaiv.

Nws yuav tsum tau muab sau tseg tias cov tshuaj lom xws li chloroform thiab sulfoxide chloride yog siv nyob rau hauv no synthesis txoj kev, thiab cov los ntawm - cov khoom generated kuj muaj tej yam toxicity. Yog li ntawd, nws yog ib qho tsim nyog yuav tsum tau ua tib zoo saib xyuas cov teeb meem kev nyab xeeb thiab txo qis ib puag ncig cov pa phem thaum lub sijhawm txheej txheem synthesis. Tsis tas li ntawd, txhawm rau kom tau txais cov khoom uas muaj purity siab, kev sib cais thiab kev ua kom huv huv yuav tsum tau ua. Kem chromatography, recrystallization, thiab lwm txoj kev tuaj yeem siv rau kev sib cais thiab ua kom huv.

Hauv qab no yog cov kauj ruam ntxaws ntxaws rau Txoj Kev 2:

Kauj Ruam 1: Nws yog ib qho tsim nyog los sib xyaw N, N-dimethylformamide (DMF) thiab 4,6-dihydroxypyrimidine (DHP) hauv qhov piv ntawm 1: 1 molar kom tau txais cov tshuaj sib xyaw.

Kauj Ruam 2: Ntxiv qhov tsim nyog ntawm cov catalyst (xws li ammonium chloride lossis triethylamine) rau cov tshuaj tov, thiab tswj cov tshuaj tiv thaiv kub ntawm 100-150 degree. Khaws qhov kub thiab txias rau ib lub sijhawm (xws li 2-3 teev) kom ua tiav cov tshuaj tiv thaiv.

Kauj Ruam 3: Txias cov tshuaj tiv thaiv rau hauv chav sov thiab ntxiv qhov tsim nyog ntawm hydrochloric acid (xws li hydrochloric acid acetic acid) rau nws kom cov tshuaj tiv thaiv acidic. Tom qab ntawd ncuav nws mus rau hauv ib qho dej uas tsim nyog thiab ntxiv cov tshuaj sodium hydroxide tsim nyog los ua cov tshuaj tiv thaiv alkaline. Nyob rau ntawm lub sijhawm no, 4,6-dichloro-5-pyrimidine formaldehyde yuav precipitate hauv daim ntawv.

Kauj Ruam 4: Lim, ntxuav, thiab ziab cov khoom ua ntej kom tau 4,6-dichloro-5-pyrimidine formaldehyde.

Cov hauv qab no yog cov tshuaj sib npaug thaum lub sij hawm ua cov txheej txheem synthesis:

N. Tom qab sib tov N-dimethylformamide nrog 4,6-dihydroxypyrimidine, cov tshuaj tiv thaiv tshwm sim los tsim 4,6-dichloro-5-pyrimidine formaldehyde:

C₄H₄N₂O₂+2N (CH₃) ₂HCOCH₃ → C₅H₃Cl₂N_1O+ N (CH₃) ₂COCH₃+H₂O

Lub luag haujlwm ntawm cov catalyst ammonium chloride lossis triethylamine yog los txhawb cov tshuaj tiv thaiv ntawm DMF thiab DHP:

C₄H₄N₂O₂+2N (CH₃) ₂HCOCH₃+2NH₄Cl → C₅H₃Cl₂N_1O+ N (CH₃) ₂COCH₃+2NH₄OH

Tom qab txias cov tshuaj tiv thaiv rau hauv chav tsev kub, ntxiv hydrochloric acid kom nws acidic, thiab ces ncuav rau hauv dej thiab ntxiv sodium hydroxide kom nws alkaline:

C₅H₃Cl₂N_1O+NaOH → C₅H₃Cl₂N_1O+ NaCl + H₂O

Los ntawm cov kauj ruam saum toj no, peb ua tiav synthesized4,6-Dichloro-5-pyrimidinecarbaldehydelos ntawm N, N-dimethylformamide thiab 4,6-dihydroxypyrimidine. Lub synthesis ntawm cov compound no yog ib qho kev sim ua kom zoo nrog cov txiaj ntsig siab txog li 95%.

4,6-Dichloro-5-pyrimidinecarbaldehydeyog ib qho organic compound feem ntau yog siv rau tsis yog - kho mob lub hom phiaj xws li kev tsim khoom lossis kev tshawb fawb tshawb fawb, thiab tsis yog tshuaj. Yog li ntawd, nruj me ntsis hais lus, tsis muaj kev cuam tshuam tsis zoo uas tau teev tseg hauv kev kho mob ib txwm muaj rau kev kho mob ntawm tib neeg lossis tsiaj txhu. Cov hauv qab no yog nws cov kev phiv tsis zoo:

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