氢化钠 → 4-((4,4-Dimethylcyclohexyl)oxy)-8-nitroquinazoline

HRID 1469731

反应方程式

HRID 1469731 反应方程式
[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1.[H-].[Na+].Cl[C:13]1[C:22]2[C:17](=[C:18]([N+:23]([O-:25])=[O:24])[CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][N:14]=1>C1COCC1>[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][CH:5]([O:8][C:13]2[C:22]3[C:17](=[C:18]([N+:23]([O-:25])=[O:24])[CH:19]=[CH:20][CH:21]=3)[N:16]=[CH:15][N:14]=2)[CH2:4][CH2:3]1

参与物

5

反应物 3

HCID 24758氢化钠HCID 1367354,4-二甲基环己-1-醇HCID 114584714-氯-8-硝基喹唑啉

产物 1

HCID 866922314-((4,4-Dimethylcyclohexyl)oxy)-8-nitroquinazoline收率 48.4%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

实验过程

To a solution of 4,4-dimethylcyclohexanol (140 mg, 1.097 mmol) in THF (2 mL) was added NaH (43 mg, 1.097 mmol, 60% in mineral oil) at 0° C. Then the reaction mixture was stirred at that temperature for 20 min and 4-chloro-8-nitroquinazoline (Intermediate-7, step 2, 115 mg, 0.549 mmol) was added to the reaction mixture. Then the reaction mixture was stirred at 0-5° C. for 4 h and then at rt for 12 h. Then the reaction mixture was quenched with water and was extracted with chloroform. The organic layer was washed with brine, separated, dried, filtered and concentrated. The residue was purified by column chromatography using chloroform to afford 80 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.89 (s, 1H), 8.49-8.46 (d, J=7.8 Hz, 1H), 8.45-8.42 (d, J=7.8 Hz, 1H), 7.86-7.80 (t, J=8.4 Hz, 1H), 5.41 (m, 1H), 1.94 (m, 2H), 1.82-1.79 (m, 2H), 1.54 (m, 2H), 1.37-1.34 (m, 2H), 0.99 (s, 3H), 0.67 (s, 3H); MS (m/z): 301.93 (M+H)+.

后处理

  1. stirringThen the reaction mixture was stirred at 0-5° C. for 4 h
  2. waitat rt for 12 h
  3. customThen the reaction mixture was quenched with water
  4. extractionwas extracted with chloroform
  5. washThe organic layer was washed with brine
  6. customseparated
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by column chromatography

来源与证据

ORD记录
ord-ffd9f05d325c445a9bed5834db9e123b
来源数据集
uspto-grants-2015_04
专利号
US09006257B2

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