Ammonium formate → HCID 59447096, compound

HRID 1746660Notes

Reaction equation

HRID 1746660 reaction equation
C([O-])=O.[NH4+].Cl[C:6]1[N:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[C:8]([N:16]([CH2:20][CH:21]2[CH2:23][CH2:22]2)[CH2:17][CH2:18][CH3:19])[N:7]=1>[Pd].O>[CH:21]1([CH2:20][N:16]([CH2:17][CH2:18][CH3:19])[C:8]2[N:7]=[CH:6][N:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=2)[CH2:22][CH2:23]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59446992HCID 59446992, compound

Product 1

HCID 59447096HCID 59447096, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A suspension of palladium on charcoal (1.2 g) in IPrOH (219 ml) was treated with a solution of (ammonium formate (12.16 g; 193 mmol) in 35 mL of water) followed by methyl 2-chloro-6-[(cyclopropylmethyl)(propyl)amino]pyrimidine-4-carboxylate (7.30 g; 25.7 mmol) and the mixture was stirred at room temperature for 1 h. The mixture was filtered through a pad of celite and rinsed with MeOH. Solvents were concentrated under vacuum. The crude was dissolved in DCM and washed with water and brine. The organic phase was dried over MgSO4, filtered and concentrated under vacuum to afford the title compound as a yellow oil (5.24 g, 81.7%).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. washrinsed with MeOH
  3. concentrationSolvents were concentrated under vacuum
  4. dissolutionThe crude was dissolved in DCM
  5. washwashed with water and brine
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-74da0327121b42029047a460cacb5f69
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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