Methanol → HCID 90112662, compound

HRID 521724Notes

Reaction equation

HRID 521724 reaction equation
[F:1][C:2]1[C:3]([O:23][CH3:24])=[N:4][C:5]([N:9]2[CH2:16][CH:15]3[C:11]([C:17]4[CH:22]=[N:21][CH:20]=[CH:19][N:18]=4)([NH:12][O:13][CH2:14]3)[CH2:10]2)=[N:6][C:7]=1[CH3:8].CO>C(O)C.[Ni].O>[NH2:12][C:11]1([C:17]2[CH:22]=[N:21][CH:20]=[CH:19][N:18]=2)[CH2:10][N:9]([C:5]2[N:4]=[C:3]([O:23][CH3:24])[C:2]([F:1])=[C:7]([CH3:8])[N:6]=2)[CH2:16][CH:15]1[CH2:14][OH:13]

Participants

6

Reactant 2

HCID 887MethanolHCID 90112022HCID 90112022, compound

Product 1

HCID 90112662HCID 90112662, compoundYield 99.3%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 5-(5-fluoro-4-methoxy-6-methyl-pyrimidin-2-yl)-6a-pyrazin-2-yl-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole (0.92 g, 2.77 mmol) in ethanol (40 mL) is hydrogenated at 50 psi in the presence of Raney nickel (as a slurry in water) (2.7 g, 45.54 mmol) for 5 hours using a PARR hydrogenator. Methanol is added and the catalyst removed by filtration through a pad of diatomaceous earth. The diatomaceous earth pad is washed with methanol. The combined filtrates are concentrated under reduced pressure to give the title compound (0.92 g, 99%). ES/MS (m/e): 335 (M+1).

Workup

  1. customfor 5 hours
  2. customthe catalyst removed by filtration through a pad of diatomaceous earth
  3. washThe diatomaceous earth pad is washed with methanol
  4. concentrationThe combined filtrates are concentrated under reduced pressure

Sources & evidence

ORD record
ord-66004be7a04d4c919cda6d874110987d
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

Loading…