Urea → 7-Methylthieno[3,2-d]pyrimidine-2,4(1H,3H)-dione

HRID 1250614Notes

Reaction equation

HRID 1250614 reaction equation
[NH2:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]=1[C:8]([O:10]C)=O.[NH2:12][C:13](N)=[O:14]>CN(C=O)C>[CH3:7][C:6]1[C:2]2[NH:1][C:13](=[O:14])[NH:12][C:8](=[O:10])[C:3]=2[S:4][CH:5]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 123584Methyl 3-amino-4-methylthiophene-2-carboxylate

Product 1

HCID 103523177-Methylthieno[3,2-d]pyrimidine-2,4(1H,3H)-dioneYield 93.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
200 °C

Procedure

To 25.0 g (146 mmol) of methyl 3-amino-4-methylthiophene-2-carboxylate was added 43.5 g (730 mmol) of urea, and the resulting mixture was heated at 200° C. for 1.5 hours. The mixture was allowed to resume room temperature, and DMF (400 ml) was added thereto, followed by heating under reflux for one hour. After completion of the reaction, ice water was added to the reaction mixture, and crystals thus precipitated were filtered to give 23.0 g (yield: 93.7%) of the title compound.

Workup

  1. customto resume room temperature
  2. temperatureby heating
  3. temperatureunder reflux for one hour
  4. additionwas added to the reaction mixture, and crystals
  5. customthus precipitated
  6. filtrationwere filtered

Sources & evidence

ORD record
ord-0eb78f1408c743c487aad66c69cc2bc5
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

Loading…