Hydrochloric Acid → 6-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-(1-methoxyethyl)pyrimidine-4-carboxylic acid

HRID 2386150Notes

Reaction equation

HRID 2386150 reaction equation
C[O:2][C:3]([C:5]1[C:10]([CH:11](F)[CH3:12])=[C:9]([NH2:14])[N:8]=[C:7]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([O:22][CH3:23])[C:16]=2[F:24])[N:6]=1)=[O:4].[OH-:25].[Na+].Cl.[CH3:28]O>>[NH2:14][C:9]1[N:8]=[C:7]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([O:22][CH3:23])[C:16]=2[F:24])[N:6]=[C:5]([C:3]([OH:2])=[O:4])[C:10]=1[CH:11]([O:25][CH3:28])[CH3:12]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 59432118HCID 59432118, compound

Product 1

HCID 594320976-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-(1-methoxyethyl)pyrimidine-4-carboxylic acidYield 85%

Procedure

6-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-(1-fluoroethyl)pyrimidine-4-carboxylic acid methyl ester (0.100 g, 0.280 mmol) was dissolved/suspended in methanol (10 mL) and 2N sodium hydroxide (0.561 mL, 1.121 mmol) was added. The reaction mixture was stirred overnight at ambient temperature, acidified with 2N HCl, and concentrated. The precipitate that formed was filtered, washed with water, and dried to provide the title compound (0.085 g, 85% yield) as a white solid, mp 165-167° C.: 1H NMR (DMSO-d6 and drop of D2O) δ 7.60 (dd, 1H), 7.39 (dd, 1H), 4.55 (q, 1H), 3.91 (s, 3H), 3.17 (s, 3H), 1.41 (dd, 3H).

Workup

  1. concentrationconcentrated
  2. customThe precipitate that formed
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-e53d1a2c02eb4b4894428751a9cda8a5
Source dataset
uspto-grants-2012_09
Patent number
US08268753B2

Reaction notes

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