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 1984111Notes

Reaction equation

HRID 1984111 reaction equation
[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

Participants

4

Reactant 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

Product 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-oxideYield 0.9%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 702EthanolSolvent2×

Procedure

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.

Sources & evidence

ORD record
ord-bb78c3fe2cc348c7ab0a4f13880526b8
Source dataset
uspto-grants-2009_06
Patent number
US07544672B2

Reaction notes

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