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

HRID 566383Notes

Reaction equation

HRID 566383 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-7f8ce20c188d414f818cf5e9796d00aa
Source dataset
uspto-grants-2001_01
Patent number
US06174889B1

Reaction notes

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