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Dimethylformamide → 2-Chloro-6-[(3S)-3-methylmorpholin-4-yl]-9-(2,2,2-trifluoroethyl)-9H-purine

HRID 1876619
ノート
印刷プレビュー

反応式

HRID 1876619 の反応式
[F:1][C:2]([F:13])([F:12])[CH2:3]OS(C(F)(F)F)(=O)=O.CN(C)C=O.[Cl:19][C:20]1[N:28]=[C:27]2[C:23]([N:24]=[CH:25][NH:26]2)=[C:22]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][C@@H:30]2[CH3:35])[N:21]=1.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:19][C:20]1[N:28]=[C:27]2[C:23]([N:24]=[CH:25][N:26]2[CH2:3][C:2]([F:13])([F:12])[F:1])=[C:22]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][C@@H:30]2[CH3:35])[N:21]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 178461593HCID 178461593、化合物

生成物 1

HCID 593335792-Chloro-6-[(3S)-3-methylmorpholin-4-yl]-9-(2,2,2-trifluoroethyl)-9H-purine収率 76.2%

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

反応条件

温度
50 °C

実験手順

2,2,2-Trifluoroethyltrifluoromethyl sulfonate (83 μl, 0.57 mmol) was added to an N,N-dimethylformamide (5 ml) suspension of 2-chloro-6-[(3S)-3-methylmorpholin-4-yl]-9H-purine (132 mg, 0.52 mmol) and potassium carbonate (86 mg, 0.62 mmol) with ice cooling. The reaction mixture was stirred at 50° C. for 2 hours and returned to room temperature. Water was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate and, after filtration, the filtrate was concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography (30% ethyl acetate:hexane) to give the title compound (133 mg, 76%) as a solid.

後処理

  1. customreturned to room temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationafter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by flash silica gel column chromatography (30% ethyl acetate:hexane)

出典と根拠

ORDレコード
ord-e07644cb64264814ac62d39cb36fddb4
出典データセット
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08309546B2

反応ノート

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