tert-Butoxy bis(dimethylamino)methane → HCID 57747322, compound

HRID 222071Notes

Reaction equation

HRID 222071 reaction equation
C[C:2]1[CH:9]=[C:8]([NH:10][C:11]2[N:16]=[C:15]([NH:17][C:18]3[C:23]([CH3:24])=[CH:22][C:21]([Br:25])=[CH:20][C:19]=3[CH3:26])[C:14]([N+:27]([O-:29])=[O:28])=[C:13]([CH3:30])[N:12]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(O[CH:36](N(C)C)[N:37]([CH3:39])[CH3:38])(C)(C)C>CN(C=O)C>[Br:25][C:21]1[CH:22]=[C:23]([CH3:24])[C:18]([NH:17][C:15]2[C:14]([N+:27]([O-:29])=[O:28])=[C:13](/[CH:30]=[CH:36]/[N:37]([CH3:39])[CH3:38])[N:12]=[C:11]([NH:10][C:8]3[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[CH:2][CH:9]=3)[N:16]=2)=[C:19]([CH3:26])[CH:20]=1

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 68805818HCID 68805818, compound

Product 1

HCID 57747322HCID 57747322, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A dried flask under argon was charged with methyl 4-(4-(4-bromo-2,6-dimethylphenylamino)-6-methyl-5-nitropyrimidin-2-ylamino)benzonitrile (4.3 g, 9.5 mmol) dissolved in anhydrous DMF (95 ml) followed by tert-butoxybis(dimethylamino)methane (2.4 ml, 11.4 mmol). The reaction mixture was heated to 60° C. and stirred overnight under argon. Upon completion the reaction was cooled to ambient temperature, concentrated to half volume, and quenched with H2O (100 ml). The aqueous solution was extracted with ethyl acetate (3×70 ml) and the collected organic fractions were washed with brine (100 ml), dried with MgSO4, filtered and concentrated. Silica gel chromatography (ethyl acetate: Hexanes=50:50) yielded (E)-4-(4-(4-bromo-2,6-dimethylphenylamino)-6-(2-(dimethylamino)vinyl)-5-nitropyrimidin-2-ylamino)benzonitrile (3.21 g, 67%) as a brown solid. m/z=508 [M+1].

Workup

  1. temperatureUpon completion the reaction was cooled to ambient temperature
  2. concentrationconcentrated to half volume
  3. customquenched with H2O (100 ml)
  4. extractionThe aqueous solution was extracted with ethyl acetate (3×70 ml)
  5. washthe collected organic fractions were washed with brine (100 ml)
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4a73ec64bd97499fbc774bef395555f4
Source dataset
uspto-grants-2012_06
Patent number
US08207178B2

Reaction notes

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