Formamidine acetate → 6-(N,N-Dimethylamino)-3H-pyrido[3,4-d]pyrimidin-4-one

HRID 2085939Notes

Reaction equation

HRID 2085939 reaction equation
[NH2:1][C:2]1[C:3]([C:11]([OH:13])=O)=[CH:4][C:5]([N:8]([CH3:10])[CH3:9])=[N:6][CH:7]=1.C(O)(=O)C.[CH:18](N)=[NH:19]>C(O)(=O)C>[CH3:10][N:8]([C:5]1[N:6]=[CH:7][C:2]2[N:1]=[CH:18][NH:19][C:11](=[O:13])[C:3]=2[CH:4]=1)[CH3:9]

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 227274305-Amino-2-(dimethylamino)isonicotinic acid

Product 1

HCID 1358174466-(N,N-Dimethylamino)-3H-pyrido[3,4-d]pyrimidin-4-oneYield 44.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Amino-2-(N,N-dimethylamino)-pyridine-4-carboxylic acid (0.54 g) was treated with formamidine acetate (3.12 g) in glacial acetic acid (20 ml) and heated at reflux for 16 hours. The mixture was cooled, evaporated to dryness in vacuo and partitioned between ethyl acetate and water. The organic phase was separated, dried over magnesium sulphate and concentrated in vacuo to give, after chromatography on silica, the title compound (0.25 g); δH CDCl3 9.10(1H,d), 8.80(1H,s), 8.31(1H,s), 7.07(1H,s), 3.20(6H,s); m/z (M+1+) 191.

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hours
  3. temperatureThe mixture was cooled
  4. customevaporated to dryness in vacuo
  5. custompartitioned between ethyl acetate and water
  6. customThe organic phase was separated
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated in vacuo
  9. customto give

Sources & evidence

ORD record
ord-1d9ef74bf37140eda579ef6d056235d9
Source dataset
uspto-grants-2004_04
Patent number
US06723726B1

Reaction notes

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