HCID 12570275, compound → HCID 20240526, compound

HRID 559739Notes

Reaction equation

HRID 559739 reaction equation
[N:1]1([C:7]2[N:12]=[C:11]([C:13]#[N:14])[CH:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-].N>CO.[Ni]>[N:1]1([C:7]2[N:12]=[C:11]([CH2:13][NH2:14])[CH:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 12570275HCID 12570275, compoundHCID 21862953Ammonia hydroxide

Product 1

HCID 20240526HCID 20240526, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-morpholin-4-yl-pyrimidine-4-carbonitrile (0.28 g, 1.47 mmol) in MeOH and 28% aqueous ammonia hydroxide (2.0 mL, 1.40 mmol) was hydrogenated over Raney-Ni catalyst using a continuous flow apparatus (conditions: 1 mL/minute, 25° C., 10 bar). After 2 hours, the solvent was concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 5% MeOH in CH2Cl2. The major fractions were combined and the solvent was concentrated in vacuo to afford the title compound.

Workup

  1. customa continuous flow apparatus (conditions: 1 mL/minute, 25° C., 10 bar)
  2. concentrationthe solvent was concentrated in vacuo
  3. customThe residue was purified by silica gel chromatography
  4. washeluting with 5% MeOH in CH2Cl2
  5. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-a8f9dd67f1ed4f278207b5b5a99e8ba6
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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