Formamide → 3H,4H-pyrido(3,4-d)pyrimidin-4-one

HRID 1059611Notes

Reaction equation

HRID 1059611 reaction equation
[NH2:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH:11]([NH2:13])=O>>[N:1]1[C:2]2[CH:10]=[N:9][CH:8]=[CH:7][C:3]=2[C:4](=[O:6])[NH:13][CH:11]=1

Participants

3

Reactant 2

HCID 713FormamideHCID 4595313-Aminoisonicotinic acid

Product 1

HCID 1355671063H,4H-pyrido(3,4-d)pyrimidin-4-oneYield 72%

Conditions

Temperature
160 °C

Procedure

A mixture of 3-amino isonicotinic acid (485 mg, 3.51 mmol) in formamide (3 mL) is heated to 160° C. for 12 h. Upon cooling, the resulting solid is filtered and washed with H2O and dried in a vacuum oven to yield 3H-pyrido[3,4-d]pyrimid-4-one (373 mg, 72%). 1H NMR (DMSO) δ 12.60 (1H, brs), 9.06 (1H, s), 8.68 (1H, d, J=5.3 Hz), 8.23 (1H, s), 7.96 (1H, d, J=5.1 Hz).

Workup

  1. temperatureUpon cooling
  2. filtrationthe resulting solid is filtered
  3. washwashed with H2O
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-52d9dcee2a1b4d6db21e7450f5f15961
Source dataset
uspto-grants-2003_02
Patent number
US06521620B1

Reaction notes

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