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

HRID 421300노트

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HRID 421300 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ca4a526d80da4d2ca55fc2e993279b5d
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097622B2

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