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 417882Notes

Reaction equation

HRID 417882 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-619b00dc309e476c94ed02eec13bd1a6
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

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