1-Acetylpiperazine → 4-(-4Acetyl piperazino)-5-(4-chlorophenylethynyl)-2-diisopropylaminomethyleneaminopyrimidine

HRID 1271033ノート

反応式

HRID 1271033 の反応式
Cl[C:2]1[C:7]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:6][N:5]=[C:4]([N:17]=[CH:18][N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[N:3]=1.[C:26]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)(=[O:28])[CH3:27]>C(#N)C>[C:26]([N:29]1[CH2:34][CH2:33][N:32]([C:2]2[C:7]([C:8]#[C:9][C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=3)=[CH:6][N:5]=[C:4]([N:17]=[CH:18][N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[N:3]=2)[CH2:31][CH2:30]1)(=[O:28])[CH3:27]

参加物

4

反応物 2

HCID 837951-AcetylpiperazineHCID 734464494-Chloro-5-(4-chlorophenylethynyl)-2-diisopropylaminomethyleneaminopyrimidine

生成物 1

HCID 685729784-(-4Acetyl piperazino)-5-(4-chlorophenylethynyl)-2-diisopropylaminomethyleneaminopyrimidine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 0.8 g of 4-chloro-5-(4-chlorophenylethynyl)-2-diisopropylaminomethyleneamino-pyrimidine, 35 mL acetonitrile and 0.71 g 1-acetyl piperazine was refluxed for one and one half hours. A green solution initially forms and the color changes to amber on continued heating. The solution was evaporated in vacuo and partitioned between dichloromethane and water. The organic phase was washed twice with water, dried over sodium sulfate, filtered and evaporated. The orange-brown brittle foam obtained was purified by column chromatography on silica gel, eluting initially with dichloromethane and then with 15% methanol/dichloromethane to give the intermediate derivative, 4-(-4-acetyl piperazino)-5-(4-chlorophenylethynyl)-2-diisopropylaminomethyleneaminopyrimidine. Heating 0.6 g of the intermediate with 40 mL methanolic ammonia in a bomb at 120° C. for 18 hours gave on evaporation in vacuo, a cocoa-colored residue which was purified by column chromatography on silica gel. The desired product 4-(4-acetylpiperazino)-2-amino-5-(4-chlorophenylethynyl)pyrimidine was obtained by elution with 5% methanol/dichloromethane, evaporation and trituration with methanol yielding 0.27 g, m.p. 165° C.

後処理

  1. temperaturewas refluxed for one and one half hours
  2. customThe solution was evaporated in vacuo
  3. custompartitioned between dichloromethane and water
  4. washThe organic phase was washed twice with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe orange-brown brittle foam obtained
  9. customwas purified by column chromatography on silica gel
  10. washeluting initially with dichloromethane

出典と根拠

ORDレコード
ord-8037ca311a3f4bc79ac2c637e2787e85
出典データセット
uspto-grants-2007_04
特許番号
US07205297B2

反応ノート

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