Sodium hydride → 1-[1-(3-Bromo-5-chloro-2-methoxy-4-methylphenyl)ethyl]-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 1499702ノート

反応式

HRID 1499702 の反応式
[H-].[Na+].[Br:3][C:4]1[C:5]([CH3:16])=[C:6]([Cl:15])[CH:7]=[C:8]([CH:12](Cl)[CH3:13])[C:9]=1[O:10][CH3:11].[CH3:17][C:18]1[C:26]2[C:21](=[N:22][CH:23]=[N:24][C:25]=2[NH2:27])[NH:20][N:19]=1>CN(C)C=O.C(Cl)Cl>[Br:3][C:4]1[C:9]([O:10][CH3:11])=[C:8]([CH:12]([N:20]2[C:21]3=[N:22][CH:23]=[N:24][C:25]([NH2:27])=[C:26]3[C:18]([CH3:17])=[N:19]2)[CH3:13])[CH:7]=[C:6]([Cl:15])[C:5]=1[CH3:16]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 866776443-Bromo-1-chloro-5-(1-chloroethyl)-4-methoxy-2-methylbenzeneHCID 178434474HCID 178434474、化合物

生成物 1

HCID 866776451-[1-(3-Bromo-5-chloro-2-methoxy-4-methylphenyl)ethyl]-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
30 °C

実験手順

Sodium hydride (36 mg, 0.91 mmol) was added to a mixture of 3-bromo-1-chloro-5-(1-chloroethyl)-4-methoxy-2-methylbenzene (150 mg, 0.503 mmol), 3-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (110 mg, 0.76 mmol) in N,N-dimethylformamide (8 mL) and the reaction was stirred at 30° C. overnight. The mixture was diluted with methylene chloride, washed with sat. NaHCO3, water, brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by silica gel chromatography, eluting with 0 to 70% EtOAc in CH2Cl2 (103 mg, 50%). LCMS calculated for C16H18BrClN5O (M+H)+: m/z=410.0; Found: 410. The racemic products were applied on a Phenomenex Lux-Cellulose 1 column (21.1×250 mm, 5 micron particle size), eluting with 5% ethanol in hexanes at a flow rate of 18 mL/min, ˜13 mg/injection, to provide two enantiomers.

後処理

  1. washwashed with sat. NaHCO3, water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel chromatography
  6. washeluting with 0 to 70% EtOAc in CH2Cl2 (103 mg, 50%)
  7. washeluting with 5% ethanol in hexanes at a flow rate of 18 mL/min, ˜13 mg/injection
  8. customto provide two enantiomers

出典と根拠

ORDレコード
ord-2472c563c2f24b0d9e939ad070f5cbee
出典データセット
uspto-grants-2015_12
特許番号
US09199982B2

反応ノート

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