Dichloromethane → 5-Bromo-3-(2,5-dichloro-pyrimidin-4-ylamino)-4-methyl-thiophene-2-carboxylic acid methylamide

HRID 1041739Notes

Reaction equation

HRID 1041739 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[S:6][CH:7]=[C:8]([CH3:19])[C:9]=1[NH:10][C:11]1[C:16]([Cl:17])=[CH:15][N:14]=[C:13]([Cl:18])[N:12]=1)=[O:4].C(Cl)Cl.[Br:23]N1C(=O)CCC1=O>CC(O)=O>[CH3:1][NH:2][C:3]([C:5]1[S:6][C:7]([Br:23])=[C:8]([CH3:19])[C:9]=1[NH:10][C:11]1[C:16]([Cl:17])=[CH:15][N:14]=[C:13]([Cl:18])[N:12]=1)=[O:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 866340193-(2,5-dichloropyrimidin-4-ylamino)-N,4-dimethylthiophene-2-carboxamide

Product 1

HCID 866340805-Bromo-3-(2,5-dichloro-pyrimidin-4-ylamino)-4-methyl-thiophene-2-carboxylic acid methylamideYield 31%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-(2,5-dichloro-pyrimidin-4-ylamino)-4-methyl-thiophene-2-carboxylic acid methylamide (0.22 g, 0.7 mmol) in 1:1 DCM:AcOH was added N-bromosuccinimide (0.37 g, 2.1 mmol). The mixture was stirred for 16 hours. Evaporation and chromatography on silica gel with 3:1 methylene chloride/ethyl acetate gave 85 mg of 5-bromo-3-(2,5-dichloro-pyrimidin-4-ylamino)-4-methyl-thiophene-2-carboxylic acid methylamide (31%): 1H NMR (300 MHz, CDCl3) δ 8.16 (s, 1H), 6.45 (br, 1H), 2.83 (d, 3H), 2.04 (s, 3H); MS (m/e): 395.1 (M+1).

Workup

  1. customEvaporation and chromatography on silica gel with 3:1 methylene chloride/ethyl acetate

Sources & evidence

ORD record
ord-44a7fd415dbc4312ab353e45b30e4cdc
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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