Bromoacetonitrile → [[4-Amino-2,6-bis[[(2,3-difluorophenyl)methyl]thio]-5-pyrimidinyl]amino]acetonitrile

HRID 1789936Notes

Reaction equation

HRID 1789936 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([NH2:17])[C:14]([NH2:18])=[C:13]([S:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=2[F:28])[N:12]=1.[CH:29]([N:32](C(C)C)CC)(C)[CH3:30].BrCC#N>CS(C)=O>[NH2:17][C:15]1[C:14]([NH:18][CH2:30][C:29]#[N:32])=[C:13]([S:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=2[F:28])[N:12]=[C:11]([S:10][CH2:9][C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[F:1])[N:16]=1

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 220370522,6-Bis[[(2,3-difluorophenyl)methyl]thio]-4,5-pyrimidinediamine

Product 1

HCID 22037045[[4-Amino-2,6-bis[[(2,3-difluorophenyl)methyl]thio]-5-pyrimidinyl]amino]acetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of the product of example 1 step a) (5.0 g), diisopropylethylamine (2.8 ml) and bromoacetonitrile (1.1 ml) in DMSO (50 ml) was heated at 100° C. for 5 hours. After cooling, the reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride. The organic phase was dried over magnesium sulphate, filtered and evaporated to give a black oil which was purified by silica gel flash column chromatography, eluting with 10:1 dichloromethane:ethyl acetate, to give the subtitled compound as a pale orange solid (1.6 g).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customto give a black oil which
  7. customwas purified by silica gel flash column chromatography
  8. washeluting with 10:1 dichloromethane

Sources & evidence

ORD record
ord-d60e4e9c520c41e3a9a992d14b316b33
Source dataset
uspto-grants-2006_07
Patent number
US07071193B2

Reaction notes

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