Ammonium formate → Methyl 6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylate

HRID 1746650Notes

Reaction equation

HRID 1746650 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([N:12]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:13][CH:14]2[CH2:16][CH2:15]2)[N:3]=1.C([O-])=O.[NH4+]>CC(O)C.O.[Pd]>[CH:17]1([N:12]([CH2:13][CH:14]2[CH2:15][CH2:16]2)[C:4]2[N:3]=[CH:2][N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 59446993Methyl 2-chloro-6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylate2×

Product 1

HCID 59446889Methyl 6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylateYield 97.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of methyl 2-chloro-6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylate (Intermediate 11, 4.77 g; 14.7 mmol) in 150 ml of iPrOH was treated with 780 mg of palladium (10% on C). The suspension was degassed and a solution of ammonium formate (6.96 g; 110 mmol) in 20 ml of water was added. After stirring at RT for 45 minutes, the suspension was filtered on a pad of Celite, the remaining residue was twice rinsed with 50 ml of iPrOH and the combined filtrates were evaporated under reduced pressure. The remaining colorless residue was partitioned between 150 ml of MTBE and 150 ml of water. Both layers were separated. The organic phase was once washed with 100 ml of brine, dried over MgSO4 and concentrated under reduced pressure to give the title compound as colorless oil (4.14 g, 97%).

Workup

  1. customThe suspension was degassed
  2. filtrationthe suspension was filtered on a pad of Celite
  3. washthe remaining residue was twice rinsed with 50 ml of iPrOH
  4. customthe combined filtrates were evaporated under reduced pressure
  5. customThe remaining colorless residue was partitioned between 150 ml of MTBE and 150 ml of water
  6. customBoth layers were separated
  7. washThe organic phase was once washed with 100 ml of brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-03132e227e5a4c389063573a25948c90
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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