Cesium carbonate → N,N,3-Trimethyl-4-((5-(pyridin-4-yl)-4-((tetrahydro-2H-pyran-4-yl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)benzamide

HRID 1487593

反応式

HRID 1487593 の反応式
Cl[C:2]1[N:3]=[C:4]([NH:25][CH:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[C:5]2[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[CH:9][N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:6]=2[N:7]=1.[NH2:32][C:33]1[CH:43]=[CH:42][C:36]([C:37]([N:39]([CH3:41])[CH3:40])=[O:38])=[CH:35][C:34]=1[CH3:44].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:41][N:39]([CH3:40])[C:37](=[O:38])[C:36]1[CH:42]=[CH:43][C:33]([NH:32][C:2]2[N:3]=[C:4]([NH:25][CH:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)[C:5]3[C:10]([C:11]4[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=4)=[CH:9][N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:23])([CH3:24])[CH3:22])[C:6]=3[N:7]=2)=[C:34]([CH3:44])[CH:35]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 167817704-amino-N,N,3-trimethylbenzamideHCID 867264302-Chloro-5-(pyridin-4-yl)-N-(tetrahydro-2H-pyran-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

生成物 1

HCID 86726431N,N,3-Trimethyl-4-((5-(pyridin-4-yl)-4-((tetrahydro-2H-pyran-4-yl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)benzamide収率 35%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

To a degassed mixture of 2-chloro-5-(pyridin-4-yl)-N-(tetrahydro-2H-pyran-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (1 equiv), 4-amino-N,N,3-trimethylbenzamide (1.2 equiv) and cesium carbonate (3 equiv) in 1,4-dioxane (0.2 M) was added palladium acetate (0.3 equiv) and 2,2′-bis-diphenylphosphanyl-[1,1′]binaphthalenyl (0.6 equiv). The reaction was stirred at 110° C. for 2 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and concentrated. The residue was purified by silica gel chromatography (0-2% DCM in MeOH) to afford the desired product (35% yield) as a yellow solid. MS (ESI) m/z 602.3 [M+1]+.

後処理

  1. temperaturethe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel chromatography (0-2% DCM in MeOH)

出典と根拠

ORDレコード
ord-08fa8645734448918e34d4a770f888fc
出典データセット
uspto-grants-2016_08
特許番号
US09428509B2

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