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

HRID 50842

Reaction equation

HRID 50842 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9]C)=O.[CH:11]([NH2:13])=O>CCO>[N:1]1[C:2]2[CH:6]=[CH:5][S:4][C:3]=2[C:7](=[O:9])[NH:13][CH:11]=1

Participants

4

Reactant 2

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

Product 1

HCID 1354174223H,4H-thieno[3,2-d]pyrimidin-4-oneYield 26%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
240 °C

Procedure

A mixture of methyl 3-aminothiophene-2-carboxylate (1 g, 6.3 mmol) and formamide (2 g) is heated at 240° C. for 10 min. Upon cooling a precipitate appeared. It is dissolved in EtOH and filtered. The filtrate is concentrated under reduced pressure and the residue is purified by silica gel chromatography eluting with 10% MeOH in CH2Cl2 to yield 3H-thieno[3,2-d]pyrimid-4-one (249 mg, 26%) as a solid. 1H NMR (DMSO) δ 12.61 (1H, brs), 8.20 (1H, s), 8.17 (1H, d, J=5 Hz), 7.42 (1H, d, J=5 Hz).

Workup

  1. temperatureUpon cooling a precipitate
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customthe residue is purified by silica gel chromatography
  5. washeluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-21551590b0f94b3e97926eeaf14e009e
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Linked notes

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