Sodium hydride → 4-((4,4-Dimethylcyclohexyl)oxy)-8-nitroquinazoline

HRID 1469731

反応式

HRID 1469731 の反応式
[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

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 136735Cyclohexanol, 4,4-dimethyl-HCID 114584714-Chloro-8-nitroquinazoline

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-ffd9f05d325c445a9bed5834db9e123b
出典データセット
uspto-grants-2015_04
特許番号
US09006257B2

関連ノート

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