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

HRID 1633491Notes

Reaction equation

HRID 1633491 reaction equation
C([O-])=O.[NH4+:4].C[O:6][C:7]([C:9]1[S:10][CH:11]=[CH:12][C:13]=1[NH:14][CH:15]=O)=O>C(N)=O>[N:14]1[C:13]2[CH:12]=[CH:11][S:10][C:9]=2[C:7](=[O:6])[NH:4][CH:15]=1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 2777636Methyl 3-(formylamino)-2-thiophenecarboxylate

Product 1

HCID 1354174223H,4H-thieno[3,2-d]pyrimidin-4-oneYield 63.4%

Reagents, catalysts & solvents 1

HCID 713FormamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of ammonium formate (9.4 g, 0.15 mol) in formamide (14 mL) at 150° C. was added 3-(formylamino)-2-thiophenecarboxylic acid methyl ester (81, 5.2 g, 28 mmol) as a solid in small portions. The resulting solution was heated at 150° C. for 4 hours and then allowed to stand at room temperature for 12 hours. The precipitate that formed was collected by vacuum filtration to give 3H-thieno[3,2-d]pyrimid-4-one (2.7 g, 63% yield) as white needles.

Workup

  1. customThe precipitate that formed
  2. filtrationwas collected by vacuum filtration

Sources & evidence

ORD record
ord-5f38312b411c49bbbb598d3439de84fd
Source dataset
uspto-grants-2003_01
Patent number
US06503914B1

Reaction notes

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