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 417882노트

반응식

HRID 417882 반응식
[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

참가 물질

4

반응물 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

생성물 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-oxide수율 0.9%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 702Ethanol용매2회

실험 절차

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.

출처 및 근거

ORD 기록
ord-619b00dc309e476c94ed02eec13bd1a6
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093229B2

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