[(2,4-Dichloropyrimidin-5-yl)methyl](4-methoxyphenyl)amine → HCID 178491934, 화합물

HRID 1243186노트

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HRID 1243186 반응식
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH2:9][NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:4][N:3]=1.C([Li])CCC.[C:24]([Si:28]([O:31][C@H:32]1[CH2:37][CH2:36][C@H:35]([N:38]=[C:39]=[O:40])[CH2:34][CH2:33]1)([CH3:30])[CH3:29])([CH3:27])([CH3:26])[CH3:25]>O1CCCC1.C(OCC)(=O)C>[C:24]([Si:28]([CH3:30])([CH3:29])[O:31][C@H:32]1[CH2:37][CH2:36][C@H:35]([N:38]2[C:6]3=[N:7][C:2]([Cl:1])=[N:3][CH:4]=[C:5]3[CH2:9][N:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[C:39]2=[O:40])[CH2:34][CH2:33]1)([CH3:27])([CH3:26])[CH3:25]

참가 물질

6

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HCID 21939303[(2,4-Dichloropyrimidin-5-yl)methyl](4-methoxyphenyl)amineHCID 178418339ButyllithiumHCID 178455365HCID 178455365, 화합물

생성물 1

HCID 178491934HCID 178491934, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
-78 °C

실험 절차

To a solution of [(2,4-dichloropyrimidin-5-yl)methyl](4-methoxy-phenyl)amine (1.0 g, 3.52 mmol) (from Example 1d supra) in tetrahydrofuran (50 mL) at −78° C. was added n-butyllithium (2.5 M in hexanes, 1.7 mL, 4.22 mmol) (Aldrich). After stirring at −78° C. for 20 minutes, tert-butyl-(trans-4-isocyanato-cyclohexyloxy)-dimethyl-silane (1.1 g, 4.22 mmol) (from Example 17b supra) was added. The mixture was stirred at −70° C. for 1 hour and then at room temperature for 3 hours. The reaction mixture was diluted with ethyl acetate, washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with ethyl acetate-hexanes (3:7 then 2:3) to give 1-[trans-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-7-chloro-3-(4-methoxy-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one. (Yield 0.61 g, 34%).

후처리

  1. stirringThe mixture was stirred at −70° C. for 1 hour
  2. waitat room temperature for 3 hours
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography
  8. washeluting with ethyl acetate-hexanes (3:7

출처 및 근거

ORD 기록
ord-c9def535b167420790bb61f77ab242e4
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115740B2

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