Formamide → 9-methoxy-4-oxo-3H-benzothieno[3,2-d]pyrimidine

HRID 1358281Notes

Reaction equation

HRID 1358281 reaction equation
[NH2:1][C:2]1[C:6]2[C:7]([O:11][CH3:12])=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[C:13]([O:15]C)=O.[CH:17]([NH2:19])=O>>[CH3:12][O:11][C:7]1[C:6]2[C:2]3[N:1]=[CH:17][NH:19][C:13](=[O:15])[C:3]=3[S:4][C:5]=2[CH:10]=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 713FormamideHCID 10799875Methyl 3-amino-4-methoxy-1-benzothiophene-2-carboxylate

Product 1

HCID 1355040769-methoxy-4-oxo-3H-benzothieno[3,2-d]pyrimidineYield 22.5%

Procedure

A mixture of methyl 3-amino-4-methoxybenzothiophene-2-carboxylate (202 mg, 0.85 mmol) and formamide (2 mL) is heated at 135 C. for 1 hr and the temperature is raised to 190 C. After 8 hr the reaction is cooled to r.t. Upon-cooling, black solid forms and is collected by filtration. The precipitate is air dried to give 9-methoxy-4-oxo-3H-benzothieno[3,2-d]pyrimidine (45 mg, 22.5%). 1H NMR (DMSO) δ12.0 (1H, brs), 8.31 (1H, s)7.70-7.55 (2H, m), 7.10 (1H, d, J=7.7 Hz), 3.97 (3H, s).

Workup

  1. temperatureis heated at 135 C
  2. temperaturethe temperature is raised to 190 C
  3. temperatureUpon-cooling
  4. filtrationblack solid forms and is collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-f0f7211a420c4e1c94d8f7b4d0816e14
Source dataset
uspto-grants-2003_07
Patent number
US06596726B1

Reaction notes

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