Methanol → HCID 57870047, compound

HRID 1045689Notes

Reaction equation

HRID 1045689 reaction equation
C([NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]([CH3:20])[C:18](=[O:21])[CH:17]=[C:16]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[N:15]=2)[CH2:10]1)C1C=CC=CC=1.C([O-])=O.[NH4+].CO>[Pd].O>[NH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]([CH3:20])[C:18](=[O:21])[CH:17]=[C:16]([C:22]3[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=3)[N:15]=2)[CH2:10]1

Participants

6

Reactant 3

HCID 887MethanolHCID 2723923Ammonium formateHCID 25004257HCID 25004257, compound

Product 1

HCID 57870047HCID 57870047, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 2-((R)-3-benzylaminopyrrolidin-1-yl)-3-methyl-6-(pyridin-4-yl)-3H-pyrimidin-4-one (1.6 g, 4.4 mmol) and ammonium formate (0.55 g, 8.9 mmol) in tatrahydrofuran (15 ml), methanol (30 ml) and water (5 ml) was added 10% palladium on charcoal (wet, 160 mg). After stirring for 4 hours at 95° C., palladium on charcoal was removed by filtration. The solvent was evaporated off under reduced pressure and the residue was partitioned between water and dichloromethane. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure to afford 2-((R)-3-aminopyrrolidin-1-yl)-3-methyl-6-(pyridin-4-yl)-3H-pyrimidin-4-one (1.0 g, 84%) as colorless crystals.

Workup

  1. custompalladium on charcoal was removed by filtration
  2. customThe solvent was evaporated off under reduced pressure
  3. customthe residue was partitioned between water and dichloromethane
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-991dbc59844c4e62b0a8cfd9fd27f95d
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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