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

HRID 1789936ノート

反応式

HRID 1789936 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d60e4e9c520c41e3a9a992d14b316b33
出典データセット
uspto-grants-2006_07
特許番号
US07071193B2

反応ノート

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