Potassium Carbonate → 3-bromo-2-(2,5-dichloro-pyrimidin-4-ylamino)-N-methyl-benzamide

HRID 1688066Notes

Reaction equation

HRID 1688066 reaction equation
[NH2:1][C:2]1[C:11]([Br:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].[Cl:13][C:14]1[N:19]=[C:18](Cl)[C:17]([Cl:21])=[CH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:12][C:11]1[C:2]([NH:1][C:16]2[C:17]([Cl:21])=[CH:18][N:19]=[C:14]([Cl:13])[N:15]=2)=[C:3]([CH:8]=[CH:9][CH:10]=1)[C:4]([NH:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 672646162-Amino-3-bromo-N-methylbenzamide

Product 1

HCID 866340743-bromo-2-(2,5-dichloro-pyrimidin-4-ylamino)-N-methyl-benzamideYield 7.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2-amino-3-bromo-N-methyl-benzamide (420 mg), 2,4,5-trichloropyrimidine (540 mg) and K2CO3 (47 mg) in DMF was heated at 85° C. overnight. The reaction mixture was loaded on silica gel, dried in vacuo, and purified by silica gel chromatography to provide 50 mg of 3-bromo-2-(2,5-dichloro-pyrimidin-4-ylamino)-N-methyl-benzamide: 1H NMR (300 MHz, CDCl3) δ 8.4 (bs, 1H), 8.3 (s, 1H), 7.8 (d, 1H), 7.6 (s, 1H), 7.3 (t, 1H), 6.3 (bs, 1H, NH), 3.0 (d, 3H).

Workup

  1. customdried in vacuo
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-8ea4171b841b4d469e75a278130f8051
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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