Formic Acid → 2,4-Diamino-5-propylpyrido[2,3-d]pyrimidine-6-carboxaldehyde

HRID 1735134

Reaction equation

HRID 1735134 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([NH2:17])[C:5]2[C:11]([CH2:12][CH2:13][CH3:14])=[C:10]([C:15]#N)[CH:9]=[N:8][C:6]=2[N:7]=1.C(O)=[O:19]>[Ni]>[NH2:1][C:2]1[N:3]=[C:4]([NH2:17])[C:5]2[C:11]([CH2:12][CH2:13][CH3:14])=[C:10]([CH:15]=[O:19])[CH:9]=[N:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 284Formic Acid2×HCID 100367322,4-Diamino-5-propylpyrido[2,3-d]pyrimidine-6-carbonitrile

Product 1

HCID 194368962,4-Diamino-5-propylpyrido[2,3-d]pyrimidine-6-carboxaldehydeYield 8%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Raney Ni (1.2 g damp) was added with the aid of 95-97% HCO2H (7 mL) to a solution of 2,4-diamino-5-propylpyrido[2,3-d]pyrimidine-6-carbonitrile (I-4a) (500 mg, 2.19 mmol) in 95-97% HCO2H (5 mL). The stirred mixture was heated at 75°-80° C. for 1.5 h. Raney Ni was removed by filtration, and the filtrate was evaporated. The residue was dissolved in hot H2O (20 mL), and the solution was filtered, then cooled, and treated with concentrated NH4OH to pH 7 to cause solid to precipitate. The mixture was kept at 0°-5° C. overnight before the solid was collected and washed with cold H2O. This crude material was applied to a silica gel column and eluted with CHCl3 --MeOH (7:1). Evaporation of the product fractions afforded the aldehyde compound 2,4-diamino-5-propylpyrido[2,3-d]pyrimidine-6-carboxaldehyde; yield 8% (41 mg).

Workup

  1. temperatureThe stirred mixture was heated at 75°-80° C. for 1.5 h
  2. customRaney Ni was removed by filtration
  3. customthe filtrate was evaporated
  4. dissolutionThe residue was dissolved in hot H2O (20 mL)
  5. filtrationthe solution was filtered
  6. temperaturecooled
  7. additiontreated with concentrated NH4OH to pH 7
  8. customto precipitate
  9. customwas collected
  10. washwashed with cold H2O
  11. washeluted with CHCl3 --MeOH (7:1)
  12. customEvaporation of the product fractions

Sources & evidence

ORD record
ord-cafe53a3ccf2438383468801d8be6848
Source dataset
uspto-grants-1996_07
Patent number
US05536724

Linked notes

Loading…