Acetic Acid → HCID 178503447, compound

HRID 619286Notes

Reaction equation

HRID 619286 reaction equation
[CH3:1][S:2][C:3](=[NH:5])[NH2:4].C(=O)([O-])[O-].[Na+].[Na+].[C:12](OCC)(=[O:17])[CH2:13][C:14]([CH3:16])=O.C(O)(=O)C>O>[OH:17][C:12]1[CH:13]=[C:14]([CH3:16])[N:4]=[C:3]([S:2][CH3:1])[N:5]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 51422-Methyl-2-thiopseudourea2×HCID 8868Ethyl AcetoacetateHCID 10340Sodium Carbonate

Product 1

HCID 178503447HCID 178503447, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

S-Methylisothiourea (22.26 g, 160 mmol) was added to a solution of sodium carbonate (16.9 g, 160 mmol) in water (50 mL) and stirred at room temperature until complete dissolution of the S-methylisothiourea. Ethyl acetoacetate (10.41 g, 80 mmol) was added to the mixture in one portion. After stirring for 60 hours at room temperature, the reaction was neutralized with acetic acid precipitating a white solid. The solid was collected, washed with water, and dried in vacuo to give 4-hydroxy-6-methyl-2-(methylthio)pyrimidine (9.38 g, 75%), m.p. 218-221° C.

Workup

  1. customThe solid was collected
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-ac4e15e1933c4775b18f51185d2ff9eb
Source dataset
uspto-grants-1999_09
Patent number
US05958934

Reaction notes

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