Ammonia hydroxide → HCID 58222741, compound

HRID 559737Notes

Reaction equation

HRID 559737 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]([CH3:14])[S:10]([CH3:13])(=[O:12])=[O:11])[N:4]=1)#[N:2].[OH-].N>CO.[Ni]>[NH2:2][CH2:1][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]([CH3:14])[S:10]([CH3:13])(=[O:12])=[O:11])[N:4]=1

Participants

5

Reactant 2

HCID 21862953Ammonia hydroxideHCID 59278443HCID 59278443, compound

Product 1

HCID 58222741HCID 58222741, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of N-(4-cyano-pyrimidin-2-yl)-N-methyl-methanesulfonamide (0.15 g, 0.71 mmol) in MeOH and 28% aqueous ammonia hydroxide (1.2 mL, 0.70 mmol) was hydrogenated over Raney-Ni catalyst using a continuous flow hydrogenation 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 hydrogenation 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-9bdf40defc1d4bebb906f9f96d781267
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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