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

HRID 1192294Notes

Reaction equation

HRID 1192294 reaction equation
C[O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:10][CH:11]=O)=O.C([O-])=O.[NH4+].C([NH2:19])=O>>[N:10]1[C:9]2[CH:8]=[CH:7][S:6][C:5]=2[C:3](=[O:2])[NH:19][CH:11]=1

Participants

4

Reactant 3

HCID 713FormamideHCID 2723923Ammonium formateHCID 2777636Methyl 3-(formylamino)-2-thiophenecarboxylate

Product 1

HCID 1354174223H,4H-thieno[3,2-d]pyrimidin-4-oneYield 74%

Conditions

Temperature
140 °C

Procedure

To a mixture of 3-formylaminothiophene-2-carboxylic acid methyl ester (20.5 g, 111 mmol) and ammonium formate (21 g, 333 mmol) was added formamide (29.8 g, 662 mmol). The slurry was heated to 140° C. for 10 hours. After cooling, the solid was filtered, washed with water and dried under vacuum to afford the product 3H-Thieno[3,2-d]pyrimidin-4-one (12.5 g, 74%). 1H NMR (DMSO, 400 Hz) δ 12.31 (br, 1H), 8.18 (d, J=5.2 Hz, 1H), 8.16 (s, 1H), 7.41 (d, J=5.2 Hz, 1H). MS (ESI+) [M+H]+ 153

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid was filtered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-21ce18eabdff4dc393bfcf6e1b020642
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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