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

HRID 245302Notes

Reaction equation

HRID 245302 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-6a96176530d846269f19cb90b8cb9086
Source dataset
uspto-grants-2014_02
Patent number
US08658791B2

Reaction notes

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