Ammonium formate → HCID 59447096, compound

HRID 1946678Notes

Reaction equation

HRID 1946678 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-576a0b84cc0e47c3a53b8a9a6efe764d
Source dataset
uspto-grants-2013_03
Patent number
US08399448B2

Reaction notes

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