tert-Butoxy bis(dimethylamino)methane → 4-(4-(4-bromo-2,6-dimethylphenylthio)-6-((E)-2-(dimethylamino)vinyl)-5-nitropyrimidin-2-ylamino)benzonitrile

HRID 222084Notes

Reaction equation

HRID 222084 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]([NH:20][C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=3)[N:11]=2)=[C:4]([CH3:29])[CH:3]=1.C(O[CH:35](N(C)C)[N:36]([CH3:38])[CH3:37])(C)(C)C>CN(C=O)C>[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](/[CH:19]=[CH:35]/[N:36]([CH3:38])[CH3:37])[N:13]=[C:12]([NH:20][C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=3)[N:11]=2)=[C:4]([CH3:29])[CH:3]=1

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 577473484-(4-(4-Bromo-2,6-dimethylphenylthio)-6-methyl-5-nitropyrimidin-2-ylamino)benzonitrile

Product 1

HCID 577473844-(4-(4-bromo-2,6-dimethylphenylthio)-6-((E)-2-(dimethylamino)vinyl)-5-nitropyrimidin-2-ylamino)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-(4-(4-bromo-2,6-dimethylphenylthio)-6-methyl-5-nitropyrimidin-2-ylamino)benzonitrile (50 mmol) in DMF (300 ml) is added tert-butoxybis(dimethylamino) methane (60 mmol) over 15 minutes. The mixture is stirred at room temperature overnight. DMF is partially removed. The residue is washed with water and extracted with ethyl acetate (×3). The combined organic layers are washed with brine, dried (MgSO4) and concentrated to dryness to give the desired product which is used in next step without further purification.

Workup

  1. customDMF is partially removed
  2. washThe residue is washed with water
  3. extractionextracted with ethyl acetate (×3)
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-347d4c6913c84c68a9d7388f2706d9ee
Source dataset
uspto-grants-2012_06
Patent number
US08207178B2

Reaction notes

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