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

HRID 1789936노트

반응식

HRID 1789936 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d60e4e9c520c41e3a9a992d14b316b33
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071193B2

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