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

反応式

HRID 542207 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-e68641a975ef4ed6a4a47b8e4d03dbc1
出典データセット
uspto-grants-1987_04
特許番号
US04656174

関連ノート

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