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

HRID 50775

Reaction equation

HRID 50775 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[CH:4][CH:3]=1.[CH:11]([NH2:13])=O>>[N:1]1[C:2]2[CH:3]=[CH:4][N:5]=[CH:6][C:7]=2[C:8](=[O:10])[NH:13][CH:11]=1

Participants

3

Reactant 2

HCID 713FormamideHCID 3199794-Aminonicotinic acid

Product 1

HCID 135471148Pyrido(4,3-d)pyrimidin-4(3H)-oneYield 47%

Procedure

Crude 4-amino nicotinic acid (2.72 g, 11.4 mmol) in formamide (20 mL) is heated to 170° C. for 12 h. The volatiles are distilled out under reduced pressure (0.8 mmHg). The residual solid is then purified on a medium pressure silica gel column, eluting with 10% MeOH in CHCl3 to give 3H-pyrido[4,3-d]pyrimidin-4-one (780 mg, 47%) as a whitish yellow solid. 1H NMR (DMSO) δ 12.64 (1H, brs), 9.28 (1H, s), 8.83 (1H, d, J=5.5 Hz), 8.30 (1H, s), 7.58 (1H, d, J=5.8 Hz).

Workup

  1. distillationThe volatiles are distilled out under reduced pressure (0.8 mmHg)
  2. customThe residual solid is then purified on a medium pressure silica gel column
  3. washeluting with 10% MeOH in CHCl3

Sources & evidence

ORD record
ord-f0dd29621f58403a98db1034a1f634e3
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Linked notes

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