N-bromobutanimide → 6-Amino-5-bromo-2-(4-chloro-2-fluoro-3-methoxyphenyl)-pyrimidine-4-carboxylic acid methyl ester

HRID 245281Notes

Reaction equation

HRID 245281 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([NH2:11])[N:8]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([O:19][CH3:20])[C:13]=2[F:21])[N:6]=1)=[O:4].[Br:22]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:10]([Br:22])=[C:9]([NH2:11])[N:8]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([O:19][CH3:20])[C:13]=2[F:21])[N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 594320836-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylic acid methyl ester

Product 1

HCID 594321166-Amino-5-bromo-2-(4-chloro-2-fluoro-3-methoxyphenyl)-pyrimidine-4-carboxylic acid methyl esterYield 77%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylic acid methyl ester (778 mg, 2.5 mmol) and N-bromosuccinimide (489 mg, 2.75 mmol) were combined in chloroform (10 mL) and heated at reflux for 12 h. The cooled reaction mixture was concentrated and the product was purified by flash chromatography on silica gel to yield the title compound (752 mg, 77% yield): mp 173-175° C.: 1H NMR (CDCl3) δ 7.66 (dd, 1H), 7.24 (dd, 1H), 5.73 (br s, 2H), 4.03 (s, 3H), 4.01 (d, 3H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 12 h
  3. customThe cooled reaction mixture
  4. concentrationwas concentrated
  5. customthe product was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-c337896fbc5a4a7cb17b2440f419168e
Source dataset
uspto-grants-2014_02
Patent number
US08658791B2

Reaction notes

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