Dimethylformamide → 7-Benzyl-3-cyclopropylmethylxanthine

HRID 323864노트

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HRID 323864 반응식
Cl.[CH2:2]([N:9]1[C:17]2[C:16](=[O:18])[NH:15]C(N)=NC=2[N:11]=[CH:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[Na+].[CH:22]1([CH2:25]Br)C[CH2:23]1.[CH3:27][N:28]([CH3:31])[CH:29]=[O:30]>O.CO>[CH2:2]([N:9]1[C:17]2[C:16](=[O:18])[NH:15][C:29](=[O:30])[N:28]([CH2:31][CH:22]3[CH2:25][CH2:23]3)[C:27]=2[N:11]=[CH:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 81503Bromomethylcyclopropane2회HCID 1356820512-Amino-7-benzyl-1,7-dihydro-6H-purin-6-one hydrochloride

생성물 1

HCID 220073157-Benzyl-3-cyclopropylmethylxanthine

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매2회

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온도
50 °C

실험 절차

A solution of 7 g (29.0 mmol) of 7-benzylxanthine from Example 6 b) in 200 ml of dimethylformamide was heated to 50° C. and treated in portions with 0.69 g (29.0) mmol of sodium hydride and stirred at 50° C. for one hour. 2.76 ml (29.0 mmol) of cyclopropylmethyl bromide were added to this suspension and the temperature was increased to 80° C. After 7 hours at 80° C., 1 ml (11.0 mmol) of cyclopropylmethyl bromide was added again. After a further 6 hours, 24 ml of water and 10 ml of methanol were added, and the mixture was allowed to stand overnight, treated again with 120 ml of water and extracted three times using 300 ml of methyl tert-butyl ether each time. The organic phases were washed with water, dried using magnesium sulfate and concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica gel column, dichloromethane/methanol (99/1).

후처리

  1. temperaturethe temperature was increased to 80° C
  2. waitAfter 7 hours at 80° C.
  3. waitAfter a further 6 hours
  4. waitto stand overnight
  5. extractionextracted three times
  6. washThe organic phases were washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by flash chromatography on a silica gel column, dichloromethane/methanol (99/1)

출처 및 근거

ORD 기록
ord-e101a7038ae74029b088eb3d222d92bc
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06214992B1

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