Hydrochloric Acid → 4-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-ethenylpyrimidine-6-carboxylic acid

HRID 245303Notes

Reaction equation

HRID 245303 reaction equation
C[O:2][C:3]([C:5]1[C:10]([CH:11]=[CH2:12])=[C:9]([NH2:13])[N:8]=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([O:21][CH3:22])[C:15]=2[F:23])[N:6]=1)=[O:4].[OH-].[Na+].Cl>CO>[NH2:13][C:9]1[N:8]=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([O:21][CH3:22])[C:15]=2[F:23])[N:6]=[C:5]([C:3]([OH:4])=[O:2])[C:10]=1[CH:11]=[CH2:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 594321224-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-ethenyl-6-methoxycarbonylpyrimidine

Product 1

HCID 468509124-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-ethenylpyrimidine-6-carboxylic acidYield 71.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-vinylpyrimidine-4-carboxylic acid methyl ester (200 mg, 0.59 mmol) was dissolved in methanol (15 mL) and 2N sodium hydroxide (1 mL, 2 mmol) was added. The reaction mixture was stirred at ambient temperature for 2 h, acidified with a slight excess of 2N HCl, and concentrated. The crystals that formed were filtered off, washed with water, washed with diethyl ether, and dried under vacuum to yield the title compound (136 mg, 71% yield): mp 167-168° C.: 1H NMR (DMSO-d6 and drop of D2O) δ 7.62 (m, 1H), 7.43 (m, 1H), 6.65 (dd, 1H), 5.67 (m, 2H), 3.92 (d, 3H).

Workup

  1. concentrationconcentrated
  2. customThe crystals that formed
  3. filtrationwere filtered off
  4. washwashed with water
  5. washwashed with diethyl ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-e75c971539f1433999331d15aa93b4f9
Source dataset
uspto-grants-2014_02
Patent number
US08658791B2

Reaction notes

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