Réaction #2075733

ord-5b8cb3e1963e480f9284bc31dc2ba1d7

Équation de réaction

COC(=O)c1nc(-c2ccc(Cl)c(OC)c2F)nc(N)c1SC
6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-methylsulfanyl-pyrimidine-4-carboxylic acid methyl ester
[Na+].[OH-]
sodium hydroxide
Cl
HCl
COc1c(Cl)ccc(-c2nc(N)c(SC)c(C(=O)O)n2)c1F
title compound
Rendement 70.6%
COc1c(Cl)ccc(-c2nc(N)c(SC)c(C(=O)O)n2)c1F
6-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-methylsulfanyl-pyrimidine-4-carboxylic acid
Rendement 70.6%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    ConcentrationThe resulting solution was concentrated
  2. 2
    Autrepartitioned between ethyl acetate and water
  3. 3
    AutreThe organic phase was dried
  4. 4
    Concentrationconcentrated

Mode opératoire

6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-methylsulfanyl-pyrimidine-4-carboxylic acid methyl ester (100 mg, 0.28 mmol) was dissolved in 2 mL methanol and 0.5 mL of 2N sodium hydroxide (1 mmol) was added. The reaction mixture was stirred at room temperature for 4 h and then acidified with a slight excess of 2N HCl. The resulting solution was concentrated and partitioned between ethyl acetate and water. The organic phase was dried and concentrated to yield the title compound (68 mg, 70% yield): mp 153° C. (dec.): 1H NMR (CDCl3): δ 7.63 (m, 1H), 7.2 (m, 1H), 6.4 (br s, 2H), 3.98 (s, 3H), 2.42 (s, 3H).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07642220B2uspto-grants-2010_01