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

HRID 1988595Notes

Reaction equation

HRID 1988595 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1.[NH3:15]>CO.CCOC(C)=O>[NH2:15][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 2226665-Pyrimidinecarboxylic acid, 4-amino-2-(methylthio)-, ethyl esterYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of ethyl 4-chloro-2-methylsulfanyl-5-pyrimidinecarboxylate (4.50 g, 19.4 mmol) in MeOH is added 7 N NH3 (13.9 mL) in MeOH at 0° C. and the mixture is stirred for 2 h at room temperature. The reaction mixture is diluted with EtOAc and washed with saturated NaHCO3 solution. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is crystallized from the mixed solvent of EtOAc and hexanes to give 2.90 g (66%) of ethyl 4-amino-2-methylsulfanyl-5-pyrimidinecarboxylate as a white solid.

Workup

  1. washwashed with saturated NaHCO3 solution
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is crystallized from the mixed solvent of EtOAc and hexanes

Sources & evidence

ORD record
ord-f486c40b271a47a9b38ba9f2ada9a4ea
Source dataset
uspto-grants-2010_01
Patent number
US07642255B2

Reaction notes

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