Formamide → 3H,4H-thieno[3,2-d]pyrimidin-4-one

HRID 252760Notes

Reaction equation

HRID 252760 reaction equation
C[O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH2:10])=O.[CH:11]([NH2:13])=O>>[N:10]1[C:9]2[CH:8]=[CH:7][S:6][C:5]=2[C:3](=[O:2])[NH:13][CH:11]=1

Participants

3

Reactant 2

HCID 713FormamideHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Product 1

HCID 1354174223H,4H-thieno[3,2-d]pyrimidin-4-oneYield 32%

Conditions

Temperature
170 °C

Procedure

Methyl-3-amino-2-thiophene carboxylate (510 mg, 3.24 mmol) was dissolved in formamide (20 ml) and heated at 170° C. 16 h. The solvent was evaporated. The crude residue was then purified by flash chromatography on silica gel (2-4% MeOH/CH2Cl2) to afford the title compound 256 (157 mg, 32% yield). LRMS: 152.0 (Calc.); 152.9 (found).

Workup

  1. custom16 h
  2. customThe solvent was evaporated
  3. customThe crude residue was then purified by flash chromatography on silica gel (2-4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-ad2932af7a2e4374905e31b7230a9f08
Source dataset
uspto-grants-2011_01
Patent number
US07868204B2

Reaction notes

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