Ammonium formate → Cyclohexyl 6-(cyclohexyloxy)pyrimidine-4-carboxylate

HRID 1746672Notes

Reaction equation

HRID 1746672 reaction equation
C([O-])=O.[NH4+].Cl[C:6]1[N:11]=[C:10]([C:12]([O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:13])[CH:9]=[C:8]([O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[N:7]=1>O.[Pd]>[CH:22]1([O:21][C:8]2[N:7]=[CH:6][N:11]=[C:10]([C:12]([O:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[O:13])[CH:9]=2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 59446909Cyclohexyl 2-chloro-6-(cyclohexyloxy)pyrimidine-4-carboxylate

Product 1

HCID 59446917Cyclohexyl 6-(cyclohexyloxy)pyrimidine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

(13.40 g; 212 mmol) in water (30 ml). A suspension of palladium on calcium carbonate (754 mg; 0.71 mmol) in IPrOH (144 ml) and was treated with 7.5 mL of ammonium formate solution and with cyclohexyl 2-chloro-6-(cyclohexyloxy)pyrimidine-4-carboxylate (4.80 g; 14.2 mmol). After 10 min, a second aliquot of 7.5 mL of ammonium formate solution was added and the mixture was stirred at room temperature for 24 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. Organic phase was dried over MgSO4, filtered off and concentrated under vacuum to afford the title compound as an orange solid without further purification.

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 materialOrganic phase was dried over MgSO4
  7. filtrationfiltered off
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3eda06a266d74fb0af0ded0d9db4ddb2
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

Loading…