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

HRID 1984109Notes

Reaction equation

HRID 1984109 reaction equation
[Cl:1][C:2]1[C:3]2[C:17]([I:18])=[CH:16][NH:15][C:4]=2[N:5]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[N:7]=1.Cl[CH2:20][C:21]1[C:26]([CH3:27])=[C:25]([O:28][CH3:29])[C:24]([CH3:30])=[CH:23][N+:22]=1[O-:31].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[C:3]2[C:17]([I:18])=[CH:16][N:15]([CH2:20][C:21]3[C:26]([CH3:27])=[C:25]([O:28][CH3:29])[C:24]([CH3:30])=[CH:23][N+:22]=3[O-:31])[C:4]=2[N:5]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:11])([CH3:12])[CH3:13])[N:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 15484841N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamideHCID 218829432-Chloromethyl-4-methoxy-3,5-dimethylpyridine 1-Oxide

Product 1

HCID 866082292-((4-chloro-5-iodo-2-pivalamido-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)-4-methoxy-3,5-dimethylpyridine 1-oxideYield 36.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide (235 mg), 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine 1-oxide (129 mg), and K2CO3 (413 mg) in DMF (6.0 mL) was stirred at rt for 3 days, and diluted with water. The precipitate was collected by filtration and washed with IPA to give 2-((4-chloro-5-iodo-2-pivalamido-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)-4-methoxy-3,5-dimethylpyridine 1-oxide (124 mg).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with IPA

Sources & evidence

ORD record
ord-511cc7e0e36844e49f861eb4806efb5a
Source dataset
uspto-grants-2009_06
Patent number
US07544672B2

Reaction notes

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