D-Psicose → HCID 86716197, compound

HRID 512170Notes

Reaction equation

HRID 512170 reaction equation
[CH:1]1([CH2:4][C:5]([C:9]2[CH:10]=[N:11][C:12]([CH:15]([F:17])[F:16])=[N:13][CH:14]=2)([CH3:8])[C:6]#[N:7])[CH2:3][CH2:2]1.N.O.OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>CO.[Ni]>[CH:1]1([CH2:4][C:5]([C:9]2[CH:10]=[N:11][C:12]([CH:15]([F:16])[F:17])=[N:13][CH:14]=2)([CH3:8])[CH2:6][NH2:7])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 441036D-PsicoseHCID 12896473Azane;hydrateHCID 86716196HCID 86716196, compound

Product 1

HCID 86716197HCID 86716197, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-cyclopropyl-2-(2-(difluoromethyl)pyrimidin-5-yl)-2-methylpropanenitrile (1 g, 4.2 mmol) and NH3.H2O (3 mL) in MeOH (20 mL) was hydrogenated with Raney Ni (1.5 g) under 50 Psi for 3 h. The reaction mixture was filtered and concentrated to give 3-cyclopropyl-2-(2-(difluoromethyl)pyrimidin-5-yl)-2-methylpropan-1-amine (1 g), which was used directly for next step.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-8db1a039f3ff4f38a878e94888b2fab6
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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