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

HRID 2063224Notes

Reaction equation

HRID 2063224 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-methoxy-phenyl)-pyrimidine-4-carboxylic acid methyl ester (778 mg, 2.5 mmol) and N-bromosuccinimide (489 mg, 2.75 mmol) were combined in chloroform and heated at reflux for 12 hours. The cooled reaction mixture was concentrated and the product was isolated by column chromatography to yield 6-amino-5-bromo-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylic acid methyl ester (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 hours
  3. customThe cooled reaction mixture
  4. concentrationwas concentrated
  5. customthe product was isolated by column chromatography

Sources & evidence

ORD record
ord-34f91dec92594596bb7787b92d17341a
Source dataset
uspto-grants-2012_10
Patent number
US08288318B2

Reaction notes

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