Chloroacetaldehyde → 7-Chloro-5-methoxyimidazo[1,2-c]pyrimidine

HRID 2164229노트

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HRID 2164229 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([O:9][CH3:10])[N:3]=1.Cl[CH2:12][CH:13]=O.C(=O)(O)[O-].[Na+].C>O.C1C=CC=CC=1>[Cl:8][C:6]1[N:5]=[C:4]([O:9][CH3:10])[N:3]2[CH:12]=[CH:13][N:1]=[C:2]2[CH:7]=1

참가 물질

7

반응물 4

HCID 33ChloroacetaldehydeHCID 297MethaneHCID 516892Sodium BicarbonateHCID 5942484-Amino-6-chloro-2-methoxypyrimidine

생성물 1

HCID 133942007-Chloro-5-methoxyimidazo[1,2-c]pyrimidine

시약·촉매·용매 2

HCID 241Benzene용매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

A mixture of 1.7 g (0.011 mole) of 4-amino-6-chloro-2-methoxypyrimidine and 3.0 g (0.015 mole) of 50% aqueous chloroacetaldehyde in 20 ml of water was heated at 80° C. for one hour, and was then cooled in an ice bath with concomitant neutralization with sodium bicarbonate. The mixture was extracted with three 50 ml portions of chloroform which were then dried over magnesium sulfate and evaporated. The residue obtained was dissolved in boiling benzene, treated with decolorizing charcoal, and filtered. The residue which was obtained by evaporation of the filtrate was triturated with diethyl ether to provide a yellow solid. The solid was purified on a preparative scale high pressure liquid chromatograph, using a mixture of 75% ethyl acetate/25% hexanes as the eluent. Recrystallization from cyclohexane gave white solid 7-chloro-5-methoxyimidazo[1,2-c]pyrimidine, m.p. 115°-118° C. Analysis: Calculated for C7H6H3OCl: %C,45.8; %H, 3.3; %N, 22.9; Found: %C,45.4; %H,3.1; %N,23.4.

후처리

  1. extractionThe mixture was extracted with three 50 ml portions of chloroform which
  2. dry with materialwere then dried over magnesium sulfate
  3. customevaporated
  4. customThe residue obtained
  5. dissolutionwas dissolved
  6. filtrationfiltered
  7. customThe residue which was obtained by evaporation of the filtrate
  8. customwas triturated with diethyl ether
  9. customto provide a yellow solid
  10. customThe solid was purified on a preparative scale high pressure liquid chromatograph
  11. additiona mixture of 75% ethyl acetate/25% hexanes as the eluent
  12. customRecrystallization from cyclohexane

출처 및 근거

ORD 기록
ord-bc5e67be57cc470dad7b00e1442f1c39
출처 데이터셋
uspto-grants-1985_03
특허 번호
US04503050

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