Methanol → 5-(but-3-en-1-ynyl)-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo [2,3-d]pyrimidin-2-amine

HRID 417883

反応式

HRID 417883 の反応式
CC1C=CC(S(O[CH2:12][CH2:13][C:14]#[C:15][C:16]2[C:24]3[C:23]([Cl:25])=[N:22][C:21]([NH2:26])=[N:20][C:19]=3[N:18]([CH2:27][C:28]3[C:33]([CH3:34])=[C:32]([O:35][CH3:36])[C:31]([CH3:37])=[CH:30][N:29]=3)[CH:17]=2)(=O)=O)=CC=1.[F-].[Cs+].CO>CN(C=O)C.C(Cl)Cl>[C:15]([C:16]1[C:24]2[C:23]([Cl:25])=[N:22][C:21]([NH2:26])=[N:20][C:19]=2[N:18]([CH2:27][C:28]2[C:33]([CH3:34])=[C:32]([O:35][CH3:36])[C:31]([CH3:37])=[CH:30][N:29]=2)[CH:17]=1)#[C:14][CH:13]=[CH2:12]

参加物

6

反応物 3

HCID 887MethanolHCID 25953Cesium fluorideHCID 866082324-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo [2,3-d]pyrimidin-5-yl)but-3-ynyl 4-methylbenzenesulfonate

生成物 1

HCID 577138135-(but-3-en-1-ynyl)-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo [2,3-d]pyrimidin-2-amine収率 79.7%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
70 °C

実験手順

A mixture of 4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo [2,3-d]pyrimidin-5-yl)but-3-ynyl 4-methylbenzenesulfonate (516 mg) and CsF (2.0 g) in DMF (7.0 mL) was heated to 70° C. for 1 h. Work-up and flash chromatography (1→3% MeOH in DCM) gave the title compound (280 mg), as a pale yellow oil. HPLC Rt=5.90 min.

出典と根拠

ORDレコード
ord-cb43ebc047014c71ba633469e0cfbeb8
出典データセット
uspto-grants-2012_01
特許番号
US08093229B2

関連ノート

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