2-Methylpyrimidin-4-amine → 5-Bromo-1-methyl-3-(2-methylpyrimidin-4-ylamino)pyridin-2(1H)-one

HRID 592888

Reaction equation

HRID 592888 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.Br[C:10]1[C:11](=[O:18])[N:12]([CH3:17])[CH:13]=[C:14]([Br:16])[CH:15]=1>>[Br:16][C:14]1[CH:15]=[C:10]([NH:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[N:7]=2)[C:11](=[O:18])[N:12]([CH3:17])[CH:13]=1

Participants

3

Reactant 2

HCID 2957632-Methylpyrimidin-4-amineHCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-one

Product 1

HCID 680968835-Bromo-1-methyl-3-(2-methylpyrimidin-4-ylamino)pyridin-2(1H)-oneYield 43.4%

Procedure

Following the procedures described in Example 196, reaction of 2-methylpyrimidin-4-amine (2.0 g, 18.3 mmol) and 3,5-dibromo-1-methylpyridin-2(1H)-one (9.6 g, 36 mmol) afforded 213a as a yellow solid (2.3 g, 43.4%). MS: [M+H]+ 295. 1H NMR (500 MHz, DMSO-d6) δ 9.20 (s, 1H), 8.78 (s, 1H), 8.26 (d, J=4.5 Hz, 1H), 7.68 (s, 1H), 7.18 (d, J=4.5 Hz, 1H), 3.59 (s, 3H), 2.52 (s, 3H).

Sources & evidence

ORD record
ord-33df10ea6a6843c0a5dabbb2e9cee633
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Linked notes

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