Dimethylformamide → 2-[2-(Isopropylamino-methyl)-pyrrolidin-1-yl]-3-methyl-6-pyridin-4-yl-5-(3-vinyl-phenyl)-3H-pyrimidin-4-one

HRID 1795452ノート

反応式

HRID 1795452 の反応式
Br[C:2]1[CH:3]=[C:4]([C:8]2[C:9](=[O:31])[N:10]([CH3:30])[C:11]([N:20]3[CH2:24][CH2:23][CH2:22][CH:21]3[CH2:25][NH:26][CH:27]([CH3:29])[CH3:28])=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:7]=1.[C:32]1(C)C(C)=CC=C[CH:37]=1.CN(C=O)C.[F-].[K+]>ClCCl>[CH:27]([NH:26][CH2:25][CH:21]1[CH2:22][CH2:23][CH2:24][N:20]1[C:11]1[N:10]([CH3:30])[C:9](=[O:31])[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH:32]=[CH2:37])[CH:3]=2)=[C:13]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[N:12]=1)([CH3:29])[CH3:28]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 7237O-XyleneHCID 522689Potassium FluorideHCID 221851765-(3-Bromo-phenyl)-2-[2-(isopropylamino-methyl)-pyrrolidin-1-yl]-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one

生成物 1

HCID 221851872-[2-(Isopropylamino-methyl)-pyrrolidin-1-yl]-3-methyl-6-pyridin-4-yl-5-(3-vinyl-phenyl)-3H-pyrimidin-4-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
140 °C

実験手順

To a 250 mL RBF, was added 5-(3-bromo-phenyl)-2-[2-(isopropylamino-methyl)-pyrrolidin-1-yl]-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one (0.48 g, 1.0 mmol), 50 mL xylene, 5 mL DMF and 0.58 mL tributhyl(vinyl)tin. The mixture was degassed by nitrogen bubbled through for 1 h. After added Pd(PPh)4 (58 mg, 0.05 mmol), the mixture was warmed up to 140° C. and stirred for 1 h under nitrogen. The mixture was cooled down to rt, 20 mL 10% KF solution was added and stirred for 30 min. The mixture was diluted with 200 mL dichloromethane, washed with sat. NaHCO3 and brine. After purified by flash chromatography, the title compound was obtained in 0.28 g as pale yellow solid. MS (ES+): 430 (M+H)+; (ES−): 428 (M−H).

後処理

  1. customThe mixture was degassed by nitrogen
  2. custombubbled through for 1 h
  3. temperatureThe mixture was cooled down to rt
  4. stirringstirred for 30 min
  5. washwashed with sat. NaHCO3 and brine
  6. customAfter purified by flash chromatography

出典と根拠

ORDレコード
ord-0ed289cdc0b3462fbeb15b3e17302beb
出典データセット
uspto-grants-2006_04
特許番号
US07026326B2

反応ノート

読み込み中…