HCID 178503485, compound → HCID 178424066, compound

HRID 1666091Notes

Reaction equation

HRID 1666091 reaction equation
[CH3:1][C:2]([CH3:30])([CH3:29])[CH2:3][N:4]([CH3:28])[C:5]1[C:10]([C:11]#[N:12])=[C:9]([NH:13][C:14]2[CH:19]=[C:18]([C:20]3[NH:24][CH:23]=[N:22][N:21]=3)[CH:17]=[CH:16][C:15]=2[CH3:25])[N:8]=[C:7](SC)[N:6]=1>C(O)C.O.O.[Ni]>[CH3:1][C:2]([CH3:30])([CH3:29])[CH2:3][N:4]([CH3:28])[C:5]1[C:10]([C:11]#[N:12])=[C:9]([NH:13][C:14]2[CH:19]=[C:18]([C:20]3[NH:24][CH:23]=[N:22][N:21]=3)[CH:17]=[CH:16][C:15]=2[CH3:25])[N:8]=[CH:7][N:6]=1

Participants

5

Reactant 1

HCID 178503485HCID 178503485, compound

Product 1

HCID 178424066HCID 178424066, compoundYield 10.5%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

To a solution of 4-[(2,2-dimethyl-propyl)-methyl-amino]-2-methylsulfanyl-6-[2-methyl-5-(4H-[1,2,4]triazol-3-yl)-phenylamino]-pyrimidine-5-carbonitrile (60 mg, 0.142 mmol) in 3 mL of 50% ethanol/water (v/v) was added 0.4 mL of 50% Raney-Ni in water solution. The solution was refluxed under argon for 18 hours. The solution was evaporated under vacuum. The resulting residue was purified by flash chromatography to afford 5.6 mg of the final product (Yield: 10%). MS (m/z) calcd for C20H24N8 (MH+), 377.2, found, 377.4.

Workup

  1. temperatureThe solution was refluxed under argon for 18 hours
  2. customThe solution was evaporated under vacuum
  3. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-c2f84a1b4dc54818bb4b3a143e2e9b97
Source dataset
uspto-grants-2011_10
Patent number
US08044040B2

Reaction notes

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