2-Chloro-N,N-dimethylpyrimidin-4-amine → 4-Amino-6,7-dimethoxy-2-[4-(4-dimethylaminopyrimidin-2-yl)piperazin-1-yl]quinoline dihydrochloride dihydrate

HRID 542207

반응식

HRID 542207 반응식
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH:3]=1.[Cl:22][C:23]1[N:28]=[C:27]([N:29]([CH3:31])[CH3:30])[CH:26]=[CH:25][N:24]=1>C(O)CCC>[OH2:12].[OH2:12].[ClH:22].[ClH:22].[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:17][CH2:18][N:19]([C:23]3[N:28]=[C:27]([N:29]([CH3:31])[CH3:30])[CH:26]=[CH:25][N:24]=3)[CH2:20][CH2:21]2)[CH:3]=1

참가 물질

4

반응물 2

HCID 959752-Chloro-N,N-dimethylpyrimidin-4-amineHCID 140689984-Amino-6,7-dimethoxy-2-(piperazin-1-yl)quinoline

생성물 1

HCID 201311224-Amino-6,7-dimethoxy-2-[4-(4-dimethylaminopyrimidin-2-yl)piperazin-1-yl]quinoline dihydrochloride dihydrate수율 25.2%

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

4-Amino-6,7-dimethoxy-2-(piperazin-1-yl)quinoline (1.26 g) and 2-chloro-4-dimethylaminopyrimidine (0.76 g) in n-butanol (60 ml) were heated under reflux for 16 hours. The mixture was then evaporated in vacuo, the residue partitioned between chloroform and sodium carbonate solution (10%) and the aqueous phase extracted with chloroform. The combined extracts were washed with water, dried (Na2SO4), evaporated in vacuo and the residue chromatographed on silica gel (Merck 9385). Elution with chloroform-methanol (100:0→95.5) followed by treatment of the product with ethereal hydrogen chloride and recrystallisation from methanol gave 4-amino-6,7-dimethoxy-2-[4-(4-dimethylaminopyrimidin-2-yl)piperazin-1-yl]quinoline dihydrochloride dihydrate (0.19 g), m.p. 260°-263°.

후처리

  1. temperatureunder reflux for 16 hours
  2. customThe mixture was then evaporated in vacuo
  3. customthe residue partitioned between chloroform and sodium carbonate solution (10%)
  4. extractionthe aqueous phase extracted with chloroform
  5. washThe combined extracts were washed with water
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customthe residue chromatographed on silica gel (Merck 9385)
  9. washElution with chloroform-methanol (100:0→95.5)
  10. customfollowed by treatment of the product with ethereal hydrogen chloride and recrystallisation from methanol

출처 및 근거

ORD 기록
ord-e68641a975ef4ed6a4a47b8e4d03dbc1
출처 데이터셋
uspto-grants-1987_04
특허 번호
US04656174

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