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

HRID 82165Notes

Reaction equation

HRID 82165 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([N:12]1[C:16]2[N:17]=[C:18]([Cl:21])[N:19]=[CH:20][C:15]=2[C:14](I)=[CH:13]1)[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:23][C:24]1[CH:25]=[N:26][CH:27]=[C:28]([CH:35]=1)[C:29](N(OC)C)=[O:30]>>[Br:23][C:24]1[CH:35]=[C:28]([C:29]([C:14]2[C:15]3[CH:20]=[N:19][C:18]([Cl:21])=[N:17][C:16]=3[N:12]([CH:10]([CH3:11])[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:13]=2)=[O:30])[CH:27]=[N:26][CH:25]=1

Participants

3

Reactant 2

HCID 184722695-Bromo-N-methoxy-N-methylpyridine-3-carboxamideHCID 866720917-(2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-2-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 86672090(5-Bromopyridin-3-yl)[7-(2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-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-methylethyl)-2-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (see Preparation 55, enantiomer 2) and 5-bromo-N-methoxy-N-methylnicotinamide to afford the title compound as a yellow solid in 30% yield, 1.4 g. 1H NMR (400 MHz, DMSO-D6) δ: −0.14 (s, 6H), 0.61 (s, 9H), 1.52 (d, 3H), 3.91-3.96 (m, 2H), 5.00 (m, 1H), 8.37 (s, 1H), 8.58 (s, 1H), 8.95 (s, 1H), 9.00 (s, 1H), 9.33 (s, 1H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-e45061741127457f95a50a9bde7665d7
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

Loading…