Dimethylformamide → 7-Benzyl-3-cyclopropylmethylxanthine

HRID 323864ノート

反応式

HRID 323864 の反応式
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

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 81503Bromomethylcyclopropane2 回HCID 1356820512-Amino-7-benzyl-1,7-dihydro-6H-purin-6-one hydrochloride

生成物 1

HCID 220073157-Benzyl-3-cyclopropylmethylxanthine

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒2 回

反応条件

温度
50 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e101a7038ae74029b088eb3d222d92bc
出典データセット
uspto-grants-2001_04
特許番号
US06214992B1

反応ノート

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