5-Bromo-N-methoxy-N-methylpyridine-3-carboxamide → (5-Bromopyridin-3-yl)[7-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-2-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl]methanone

HRID 82160Notes

Reaction equation

HRID 82160 reaction equation
[Si:1]([O:8][CH2:9][C:10]([N:13]1[C:17]2[N:18]=[C:19]([Cl:22])[N:20]=[CH:21][C:16]=2[C:15](I)=[CH:14]1)([CH3:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:24][C:25]1[CH:26]=[N:27][CH:28]=[C:29]([CH:36]=1)[C:30](N(OC)C)=[O:31]>>[Br:24][C:25]1[CH:36]=[C:29]([C:30]([C:15]2[C:16]3[CH:21]=[N:20][C:19]([Cl:22])=[N:18][C:17]=3[N:13]([C:10]([CH3:12])([CH3:11])[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:14]=2)=[O:31])[CH:28]=[N:27][CH:26]=1

Participants

3

Reactant 2

HCID 184722695-Bromo-N-methoxy-N-methylpyridine-3-carboxamideHCID 866720847-(1-((Tert-butyldimethylsilyl)oxy)-2-methylpropan-2-YL)-2-chloro-5-iodo-7H-pyrrolo[2,3-D]pyrimidine

Product 1

HCID 86672086(5-Bromopyridin-3-yl)[7-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-2-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl]methanone

Procedure

The title compound was prepared according to the method described for Preparation 28 using 7-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-2-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (see Preparation 44) and 5-bromo-N-methoxy-N-methylnicotinamide to afford the title compound as a yellow solid in 42% yield, 1.40 g.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-826b2e4f2b0f40c99d31fffe50b9f7b2
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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