Formamide → 8-Oxa-3,5-diazatricyclo[7.4.0.0,2,7]trideca-1(13),2(7),3,9,11-pentaen-6-one

HRID 1489620Notes

Reaction equation

HRID 1489620 reaction equation
[NH2:1][C:2]1[C:3]2[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=2[O:5][C:6]=1[C:7](OC)=[O:8].[CH:15]([NH2:17])=O>>[N:1]1[C:2]2[C:3]3[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=3[O:5][C:6]=2[C:7](=[O:8])[NH:17][CH:15]=1

Participants

3

Reactant 2

HCID 713FormamideHCID 674268Methyl 3-amino-1-benzofuran-2-carboxylate

Product 1

HCID 1354154698-Oxa-3,5-diazatricyclo[7.4.0.0,2,7]trideca-1(13),2(7),3,9,11-pentaen-6-oneYield 46.6%

Conditions

Temperature
25 °C

Procedure

A solution of methyl 3-aminobenzo[b]furan-2-carboxylate (0.28 g, 1.36 mmol) in formamide (5 mL) is heated at 135 C. for 4 h, then the temperature is raised to 170 C. After 4 h the reaction is cooled to 25° C. and a dark purple solid precipitates. The solid is collected by vacuum filtration and air dried to give 3H-benzofurano[3,2-d]pyrimid-4-one (118 mg, 46.6%). 1H NMR (DMSO) δ13.0 (1H, brs), 8.25 (1H, s), 8.05 (1H, d, J =8.1 Hz), 7.84 (1H, d, J=8.3 Hz), 7.68 (1H, t, J=7.7 Hz), 7.51 (1H, t, J=7.7 Hz).

Workup

  1. temperaturethe temperature is raised to 170 C
  2. customa dark purple solid precipitates
  3. filtrationThe solid is collected by vacuum filtration and air
  4. customdried

Sources & evidence

ORD record
ord-ab1765a37f9f49eab9a59e3ea8677f35
Source dataset
uspto-grants-1997_10
Patent number
US05679683

Reaction notes

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