Formamidine acetate → 1H-pyrido[3,4-d]pyrimidin-4-one

HRID 1784375Notes

Reaction equation

HRID 1784375 reaction equation
[NH2:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(O)(=O)C.[CH:15](N)=[NH:16].C(=O)(O)[O-].[Na+]>CC(N(C)C)=O>[N:1]1[C:2]2[CH:10]=[N:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[N:16][CH:15]=1

Participants

5

Reactant 3

HCID 160693Formamidine acetateHCID 4595313-Aminoisonicotinic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 1785180321H-pyrido[3,4-d]pyrimidin-4-oneYield 87.63%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-amino-isonicotinic acid (32)(26.24 g, 190.0 mmol) and formamidine acetate (39.56 g, 380 mmol) in dimethylacetamide (100 ml) was stirred and heated to 150° C. The reaction was maintained at this temperature with stirring for 12 hours before it was allowed to cool to 25° C. and then basified with sodium bicarbonate solution (5% aqueous) until pH 7-8 was attained. The resultant pale brown solid was removed by filtration, washed with water (20 ml) and dried in a desiccator to give the desired compound (24.50 g, 87.63%) which required no further purification. m/z (LC-MS, ESP): 148 [M+H]+, R/T=1.09 mins.

Workup

  1. temperatureThe reaction was maintained at this temperature
  2. stirringwith stirring for 12 hours before it
  3. temperatureto cool to 25° C.
  4. customThe resultant pale brown solid was removed by filtration
  5. washwashed with water (20 ml)
  6. customdried in a desiccator

Sources & evidence

ORD record
ord-032bca659f594568b03efd61c7c2bb57
Source dataset
uspto-grants-2009_03
Patent number
US07504397B2

Reaction notes

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