Dimethylformamide → 2-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purine

HRID 421300ノート

反応式

HRID 421300 の反応式
C(=O)([O-])[O-].[K+].[K+].[CH:7]1([CH2:10]Br)[CH2:9][CH2:8]1.CN(C)C=O.[Cl:17][C:18]1[N:26]=[C:25]2[C:21]([N:22]=[CH:23][NH:24]2)=[C:20]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[N:19]=1>C(OCC)(=O)C>[Cl:17][C:18]1[N:26]=[C:25]2[C:21]([N:22]=[CH:23][N:24]2[CH2:10][CH:7]2[CH2:9][CH2:8]2)=[C:20]([N:27]2[CH2:28][CH2:29][O:30][CH2:31][CH2:32]2)[N:19]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 32746034-(2-chloro-9H-purin-6-yl)morpholine

生成物 1

HCID 593335522-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purine収率 70.3%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

Potassium carbonate (36.0 g, 260.5 mmol) and cyclopropylmethyl bromide (20.2 g, 143.3 mmol) were added to an N,N-dimethylformamide suspension (400 ml) of 2-chloro-6-morpholin-4-yl-9H-purine (32.4 g; purity, approx. 96%; 130.2 mmol) at room temperature and the resulting mixture was stirred at 80° C. for 3 hours in a nitrogen atmosphere. The reaction mixture was left standing to cool, then poured into ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the resulting solid was washed with diethyl ether and collected by filtration to give the title compound (26.9 g, 70%) as a colorless acicular crystal. The mother liquor was further concentrated by the same procedure to give the secondary crystal of the title compound (7.68 g, 20%) as a white solid.

後処理

  1. waitThe reaction mixture was left
  2. temperatureto cool
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. washthe resulting solid was washed with diethyl ether
  8. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-ca4a526d80da4d2ca55fc2e993279b5d
出典データセット
uspto-grants-2012_01
特許番号
US08097622B2

反応ノート

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