2-((4-chloro-5-(4-hydroxybut-1-ynyl)-2-pivalamido-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)-4-methoxy-3,5-dimethylpyridine 1-oxide → 2-((2-amino-4-chloro-5-(4-hydroxybut-1-ynyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)-4-methoxy-3,5-dimethylpyridine 1-oxide

HRID 417882ノート

反応式

HRID 417882 の反応式
[Cl:1][C:2]1[C:3]2[C:17]([C:18]#[C:19][CH2:20][CH2:21][OH:22])=[CH:16][N:15]([CH2:23][C:24]3[C:29]([CH3:30])=[C:28]([O:31][CH3:32])[C:27]([CH3:33])=[CH:26][N+:25]=3[O-:34])[C:4]=2[N:5]=[C:6]([NH:8]C(=O)C(C)(C)C)[N:7]=1>CCO.[Cl-].[Cl-].[Zn+2]>[NH2:8][C:6]1[N:7]=[C:2]([Cl:1])[C:3]2[C:17]([C:18]#[C:19][CH2:20][CH2:21][OH:22])=[CH:16][N:15]([CH2:23][C:24]3[C:29]([CH3:30])=[C:28]([O:31][CH3:32])[C:27]([CH3:33])=[CH:26][N+:25]=3[O-:34])[C:4]=2[N:5]=1

参加物

4

反応物 1

HCID 866082312-((4-chloro-5-(4-hydroxybut-1-ynyl)-2-pivalamido-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)-4-methoxy-3,5-dimethylpyridine 1-oxide

生成物 1

HCID 866082302-((2-amino-4-chloro-5-(4-hydroxybut-1-ynyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)-4-methoxy-3,5-dimethylpyridine 1-oxide収率 0.9%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 702Ethanol溶媒2 回

実験手順

Crude 2-((4-chloro-5-(4-hydroxybut-1-ynyl)-2-pivalamido-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)-4-methoxy-3,5-dimethylpyridine 1-oxide (291 mg) was dissolved in 10 mL EtOH. An aliquot of this solution (2 mL) was further diluted with EtOH (5 mL) and treated with ZnCl2 (103 mg) at 120° C. for 20 min in a microwave oven. Reverse-phase preparative HPLC gave the title compound (2.2 mg), as a solid. HPLC Rt=4.88 min.

出典と根拠

ORDレコード
ord-619b00dc309e476c94ed02eec13bd1a6
出典データセット
uspto-grants-2012_01
特許番号
US08093229B2

反応ノート

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