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

HRID 1773513

Reaction equation

HRID 1773513 reaction equation
Cl[C:2](Cl)(Cl)[C:3]([N:5]=[C:6]=[O:7])=[O:4].[NH2:10][C:11]1[C:15]([CH3:16])=[CH:14][S:13]C=1C(OC)=O>C(#N)C>[CH3:16][C:15]1[C:11]2[NH:10][C:6](=[O:7])[NH:5][C:3](=[O:4])[C:2]=2[S:13][CH:14]=1

Participants

4

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 123584Methyl 3-amino-4-methylthiophene-2-carboxylate

Product 1

HCID 103523177-Methylthieno[3,2-d]pyrimidine-2,4(1H,3H)-dioneYield 57.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Trichloroacetyl isocyanate (2.0 g) was added to a solution of methyl 3-amino-4-methylthiophene-2-carboxylate (1.3 g) in acetonitrile (10 mL) and the resulting mixture was stirred for 15 minutes. The solid, which crashed out, was collected by filtration and suspended in methanol (5 mL), a solution of ammonia in methanol (7 M, 5 mL) was then added and the resulting mixture was heated at 70° C. for 15 minutes. The reaction mixture was cooled, the solid formed was collected by filtration, dried under reduced pressure to give 0.8 g of 7-methyl-1H-thieno[3,2-d]pyrimidine-2,4-dione.

Workup

  1. filtrationwas collected by filtration
  2. additiona solution of ammonia in methanol (7 M, 5 mL) was then added
  3. temperatureThe reaction mixture was cooled
  4. customthe solid formed
  5. filtrationwas collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-218b4a2c57344b62b9fb03efb34e62c9
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Linked notes

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