Isopropanol → HCID 178429770, compound

HRID 1419809Notes

Reaction equation

HRID 1419809 reaction equation
[H-].[Na+].[CH3:3][C:4]1([C@@H:7]2[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][CH2:8]2)[CH2:6][CH2:5]1.Cl[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[CH:17][N:16]=1.C(O)(C)C>O1CCCC1.O>[CH3:3][C:4]1([C@@H:7]2[CH2:12][CH2:11][C@H:10]([O:13][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=[CH:17][N:16]=3)[CH2:9][CH2:8]2)[CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 788644-ChloroquinazolineHCID 178429771HCID 178429771, compound

Product 1

HCID 178429770HCID 178429770, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

0.32 g (10.8 mmol) of sodium hydride (80% dispersion in mineral oil) was added to a solution of 1.7 g (7.9 mmol) of cis-4-(1-methylcyclopropyl)cyclohexanol in 20 ml of tetrahydrofuran, and the mixture was heated under reflux for 3 hours. It was then cooled to room temperature, 1.2 g (7.2 mmol) of 4-chloroquinazoline dissolved in 5 ml of tetrahydrofuran were added, and the mixture was heated under reflux for 2 hours. After cooling to room temperature, isopropanol was added to the reaction solution, which was subsequently stirred for 15 minutes and poured into water, after which extraction was carried out with diethyl ether. The organic phase was dried and concentrated. The residue was purified by chromatography on silica gel with petroleum ether/ethyl acetate 3:1. 1.2 g (62% of theory) were obtained of a colorless oil, which gradually solidified.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. additionwere added
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 2 hours
  6. temperatureAfter cooling to room temperature
  7. extractionafter which extraction
  8. customThe organic phase was dried
  9. concentrationconcentrated
  10. customThe residue was purified by chromatography on silica gel with petroleum ether/ethyl acetate 3:1
  11. custom1.2 g (62% of theory) were obtained of a colorless oil, which

Sources & evidence

ORD record
ord-564211554ebc4946a1fea94f36a5284a
Source dataset
uspto-grants-1999_03
Patent number
US05889012

Reaction notes

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