m-Toluidine → 4-Methyl-6-[(3-methylphenyl)amino]-2-(methylthio)-5-pyrimidinecarbonitrile

HRID 390048Notes

Reaction equation

HRID 390048 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[N:5]=[C:4]([S:11][CH3:12])[N:3]=1.[CH3:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17].C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:10][C:6]1[C:7]([C:8]#[N:9])=[C:2]([NH:17][C:16]2[CH:18]=[CH:19][CH:20]=[C:14]([CH3:13])[CH:15]=2)[N:3]=[C:4]([S:11][CH3:12])[N:5]=1

Participants

5

Reactant 3

HCID 7934m-ToluidineHCID 81531DiisopropylethylamineHCID 582963084-Chloro-6-methyl-2-(methylthio)pyrimidine-5-carbonitrile

Product 1

HCID 582963344-Methyl-6-[(3-methylphenyl)amino]-2-(methylthio)-5-pyrimidinecarbonitrileYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-chloro-6-methyl-2-(methylthio)-5-pyrimidinecarbonitrile (500 mg, 2.51 mmol) in DMF (6 mL) were added 3-methylaniline (322 mg, 3.01 mmol) and diisopropyl ethylamine (712 mg, 5.52 mmol), and the reaction mixture was stirred 70° C. for 1.5 h. The mixture was cooled and concentrated, and the residue was dissolved into EtOAc (30 mL) and washed with water (10 mL). The ethyl acetate extract was dried over Na2SO4, filtered, and concentrated. The residue was purified using column chromatography (silica gel, hexane/EtOAc, 0 to 100%) to give the product (650 mg, 96% yield).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. dissolutionthe residue was dissolved into EtOAc (30 mL)
  4. washwashed with water (10 mL)
  5. extractionThe ethyl acetate extract
  6. dry with materialwas dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified

Sources & evidence

ORD record
ord-6f6868026b7247218587679230533392
Source dataset
uspto-grants-2013_02
Patent number
US08383635B2

Reaction notes

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