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

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

Reactant 2

HCID 713Formamide

HCID 4595313-Aminoisonicotinic acid

Product 1

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

Conditions

Temperature: 16 °C

Procedure

A mixture of 3-amino isonicotinic acid (485 mg, 3.51 mmol) in formamide (3 mL) is heated to 16° 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

temperatureUpon cooling
filtrationthe resulting solid is filtered
washwashed with H2O
customdried in a vacuum oven

Sources & evidence

ORD record: ord-4aec4fe558484ab282989b0995cedcad
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713484B2

Reaction notes

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