Pyridine → 4-(4-(4-Bromo-2,6-dimethylphenylthio)-6-methyl-5-nitropyrimidin-2-ylamino)benzonitrile

HRID 222083Notes

Reaction equation

HRID 222083 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9][C:10]2[C:15]([N+:16]([O-:18])=[O:17])=[C:14]([CH3:19])[N:13]=[C:12](Cl)[N:11]=2)=[C:4]([CH3:21])[CH:3]=1.[NH2:22][C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1.N1C=CC=CC=1>C1COCC1.CO>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9][C:10]2[C:15]([N+:16]([O-:18])=[O:17])=[C:14]([CH3:19])[N:13]=[C:12]([NH:22][C:23]3[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=3)[N:11]=2)=[C:4]([CH3:21])[CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 133964-AminobenzonitrileHCID 57747345HCID 57747345, compound

Product 1

HCID 577473484-(4-(4-Bromo-2,6-dimethylphenylthio)-6-methyl-5-nitropyrimidin-2-ylamino)benzonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(4-bromo-2,6-dimethylphenylthio)-2-chloro-6-methyl-5-nitropyrimidine (59 mmol), 4-aminobenzonitrile (65 mmol) and pyridine (59 mmol) in THF (300 ml) is heated to 80° C. for 10 hours. The reaction mixture is dissolved in methanol, washed with brine and extracted with ethyl acetate. The organic layer is washed twice with brine, dried over MgSO4 and concentrated to dryness. The solid is washed with a mixture of hexane:ethyl acetate (80:20) before filtration. After filtration, the solid is washed again with methanol. The filtrate may be concentrated and additional rounds of precipitation performed following the same procedure, until all product is recovered. The combined solids are recrystallized from acetone.

Workup

  1. washwashed with brine
  2. extractionextracted with ethyl acetate
  3. washThe organic layer is washed twice with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness
  6. washThe solid is washed with a mixture of hexane:ethyl acetate (80:20) before filtration
  7. filtrationAfter filtration
  8. washthe solid is washed again with methanol
  9. concentrationThe filtrate may be concentrated
  10. customadditional rounds of precipitation
  11. customuntil all product is recovered
  12. customThe combined solids are recrystallized from acetone

Sources & evidence

ORD record
ord-658dd4259d944edd9568cabcbaaa3a44
Source dataset
uspto-grants-2012_06
Patent number
US08207178B2

Reaction notes

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