Acetone → 5-Pyrimidinol, hexahydro-2,2-dimethyl-5-phenyl-

HRID 623203Notes

Reaction equation

HRID 623203 reaction equation
Cl.Cl.[OH:3][C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH2:7][NH2:8])[CH2:5][NH2:6].[OH-].[Na+].[CH3:17][C:18]([CH3:20])=O>O>[CH3:17][C:18]1([CH3:20])[NH:8][CH2:7][C:4]([OH:3])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][NH:6]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 21290601HCID 21290601, compound

Product 1

HCID 30874705-Pyrimidinol, hexahydro-2,2-dimethyl-5-phenyl-Yield 68.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.4 g (0.01841 mol) of the dihydrochloride obtained in stage (c) above are dissolved in 50 ml of water. 2.2 g of sodium hydroxide pellets and 3 ml of acetone are added. The mixture is left to stand overnight at room temperature (15°-20° C.) and extracted with 3×100 ml of CHCl3, and the chloroform phase is washed with 30 ml of water, dried over MgSO4 and then filtered to remove MgSO4. The filtrate is evaporated to dryness; recrystallization from petroleum ether (fraction boiling at 45°-60° C.) gives 2.6 g (yield: 68.5%) of CRL 41 365. M.p.=108° C.

Workup

  1. waitThe mixture is left
  2. extraction(15°-20° C.) and extracted with 3×100 ml of CHCl3
  3. washthe chloroform phase is washed with 30 ml of water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customto remove MgSO4
  7. customThe filtrate is evaporated to dryness
  8. customrecrystallization from petroleum ether (fraction boiling at 45°-60° C.)
  9. customgives 2.6 g (yield: 68.5%) of CRL 41 365

Sources & evidence

ORD record
ord-3a4322d0a09041559f0772612c7e895d
Source dataset
uspto-grants-1988_09
Patent number
US04774248

Reaction notes

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