Dimethyl acetylsuccinate → HCID 178433551, compound

HRID 1682534Notes

Reaction equation

HRID 1682534 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[C:5]([CH:8]([CH2:13][C:14]([O:16]C)=[O:15])[C:9](OC)=[O:10])(=O)[CH3:6].[Na]>CO>[OH:10][C:9]1[C:8]([CH2:13][C:14]([OH:16])=[O:15])=[C:5]([CH3:6])[N:4]=[C:2]([SH:3])[N:1]=1

Participants

5

Reactant 3

HCID 112039Dimethyl acetylsuccinateHCID 2723790ThioureaHCID 5360545Sodium

Product 1

HCID 178433551HCID 178433551, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thiourea (80 g, 1.05 mol) and dimethyl acetylsuccinate (188 g, 1.0 mol) are added at room temperature to a solution of sodium (46 g, 2.0 mol) in methanol (800 ml). The reaction mixture is refluxed for 14 hours. The crystalline precipitate is filtered and added with stirring to a concentrated aqueous solution of hydrochloric acid (250 ml). The resulting colorless crystalline precipitate is filtered, washed with methanol and dried at high vacuum to give 4-hydroxy-2-mercapto-6-methyl-5-pyrimidinyl acetic acid (190 g, 95%). 1H-NMR (DMSO):12.4 (s, 1H); 12.3 (s, 1H); 3.4 (s, 2H); 2.1 (s, 3H).

Workup

  1. temperatureThe reaction mixture is refluxed for 14 hours
  2. filtrationThe crystalline precipitate is filtered
  3. additionadded
  4. filtrationThe resulting colorless crystalline precipitate is filtered
  5. washwashed with methanol
  6. customdried at high vacuum

Sources & evidence

ORD record
ord-0fb3772623d44fdfb89671936dee9a93
Source dataset
uspto-grants-1997_06
Patent number
US05635508

Reaction notes

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