Ammonium Hydroxide → 5-Pyrimidinecarboxylic acid, 4-amino-2-(methylthio)-, ethyl ester

HRID 522710

Reaction equation

HRID 522710 reaction equation
[OH-].[NH4+:2].Cl[C:4]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][N:7]=[C:6]([S:15][CH3:16])[N:5]=1>C(O)C>[NH2:2][C:4]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][N:7]=[C:6]([S:15][CH3:16])[N:5]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 2226665-Pyrimidinecarboxylic acid, 4-amino-2-(methylthio)-, ethyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add concentrated ammonium hydroxide (335 mL, 8.60 mol) to a vigorously stirred suspension of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (200 g, 860 mmol) in ethanol (EtOH) (450 mL) and allow to stir overnight. Collect the solids by filtration, rinse with EtOH (2×100 mL) and H2O (3×200 mL) and dry in a vacuum oven (65-70° C.) overnight to afford the title compound (164.4 g, 90% yield) as a white solid. MS (m/z): 214.1 (M+1).

Workup

  1. customCollect the solids
  2. filtrationby filtration
  3. washrinse with EtOH (2×100 mL) and H2O (3×200 mL)
  4. customdry in a vacuum oven (65-70° C.) overnight

Sources & evidence

ORD record
ord-4e58a5e0242642739bfd02531306943d
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Linked notes

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