Pyridine → HCID 68805818, compound

HRID 386626Notes

Reaction equation

HRID 386626 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH: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=C[CH:32]=1>C1COCC1>[CH3:32][C:29]1[CH:30]=[C:23]([NH:22][C:12]2[N:11]=[C:10]([NH:9][C:5]3[C:6]([CH3:8])=[CH:7][C:2]([Br:1])=[CH:3][C:4]=3[CH3:21])[C:15]([N+:16]([O-:18])=[O:17])=[C:14]([CH3:19])[N:13]=2)[CH:24]=[CH:25][C:26]=1[C:27]#[N:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 133964-AminobenzonitrileHCID 57747352HCID 57747352, compound

Product 1

HCID 68805818HCID 68805818, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(4-bromo-2,6-dimethylphenyl)-2-chloro-6-methyl-5-nitropyrimidin-4-amine (18.5 g, 49.8 mmol) and 4-aminobenzonitrile (5.9 g, 49.8 mmol) in THF (250 ml) at ambient temperature was added pyridine (4.0 ml, 49.8 mmol). The reaction mixture was heated to reflux and stirred for 2 days under argon. Upon completion half of the solvent was removed in vacuo. The solids were dissolved in methanol and 250 ml brine was added. The aqueous layer was extracted with ethyl acetate (3×125 ml) and the collected organic fractions were dried with MgSO4, filtered and reduced in vacuo. The resulting solids were slurried in methanol and Et2O and filtered. The filtrand was washed 3× with cold Et2O and dried overnight under vacuum to give 14.4 g (64%) of methyl 4-(4-(4-bromo-2,6-dimethylphenylamino)-6-methyl-5-nitropyrimidin-2-ylamino)benzonitrile as a brown powder. m/z=453 [M+1].

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. customUpon completion half of the solvent was removed in vacuo
  4. dissolutionThe solids were dissolved in methanol
  5. addition250 ml brine was added
  6. extractionThe aqueous layer was extracted with ethyl acetate (3×125 ml)
  7. dry with materialthe collected organic fractions were dried with MgSO4
  8. filtrationfiltered
  9. filtrationEt2O and filtered
  10. washThe filtrand was washed 3× with cold Et2O
  11. customdried overnight under vacuum

Sources & evidence

ORD record
ord-2183a891265c4b999bd56b78f09c0331
Source dataset
uspto-grants-2013_02
Patent number
US08372852B2

Reaction notes

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