Réaction #1994295

ord-6116a2f461b7439fb91de92c1ec53b8e

Équation de réaction

COC(=O)c1cc(N)nc(-c2cc(F)c(Cl)cc2F)n1
6-Amino-2-(4-chloro-2,5-difluorophenyl)pyrimidine-4-carboxylic acid methyl ester
O=C1CCC(=O)N1Cl
N-chlorosuccinimide
COC(=O)c1nc(-c2cc(F)c(Cl)cc2F)nc(N)c1Cl
title compound
Rendement 50.0%
COC(=O)c1nc(-c2cc(F)c(Cl)cc2F)nc(N)c1Cl
6-Amino-5-chloro-2-(4-chloro-2,5-difluorophenyl)-pyrimidine-4-carboxylic acid methyl ester
Rendement 50.0%

Solvants

Conditions de réaction

Température
40°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    ConcentrationThe reaction mixture was concentrated
  2. 2
    Autrethe product purified by column chromatography (ethyl acetate/hexane gradient)

Mode opératoire

6-Amino-2-(4-chloro-2,5-difluorophenyl)pyrimidine-4-carboxylic acid methyl ester (0.090 g, 0.3 mmol) and N-chlorosuccinimide (0.05 g, 0.37 mmol) were combined in 10 mL acetonitrile and heated at 40° C. for 18 hours. The reaction mixture was concentrated and the product purified by column chromatography (ethyl acetate/hexane gradient) to yield the title compound as an off-white solid (0.050 g, 50% yield): 1H NMR (CDCl3): δ 7.85 (dd, 1H), 7.22 (dd, 1H), 5.62 (br s, 2H), 4.01 (s, 3H).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08598085B2uspto-grants-2013_12