Formamide → 4-Hydroxypyrido (2,3-d)pyrimidine

HRID 50831

Reaction equation

HRID 50831 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH:11]([NH2:13])=O>>[N:1]1[C:2]2[N:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4](=[O:6])[NH:13][CH:11]=1

Participants

3

Reactant 2

HCID 713FormamideHCID 729302-Aminonicotinic acid

Product 1

HCID 1354402774-Hydroxypyrido (2,3-d)pyrimidine

Procedure

2-Amino nicotinic acid (15 g, 108.6 mmol) in formamide (35 mL) is heated to 165 −170° C. for 3.5 h. Upon cooling a solid precipitates. The solid is filtered and washed with H2O and dried in a vacuum oven to give 3H-pyrido[2,3-d]pyrimidin-4-one (7.87 g, 49.4). 1H NMR (DMSO) δ 12.50 (1H, s), 8.97 (1H, dd, J=1.9, 4.5 Hz), 8.53 (1H, dd, J=2.1, 7.9 Hz), 8.34 (1H, s), 7.57 (1H, dd, J=4.6, 8.0 Hz).

Workup

  1. temperatureUpon cooling a solid
  2. customprecipitates
  3. filtrationThe solid is filtered
  4. washwashed with H2O
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-16466fd53fde427f990b44b3d26336cd
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Linked notes

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