Water → 2,2,4,4,6-Pentamethylhexahydropyrimidine

HRID 1995419Notes

Reaction equation

HRID 1995419 reaction equation
[CH3:1][C:2]1([CH3:11])[NH:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4]([CH3:10])=[N:3]1.[Na].O>C(O)C>[CH3:1][C:2]1([CH3:11])[NH:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH:4]([CH3:10])[NH:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 68396Pyrimidine, 1,2,5,6-tetrahydro-2,2,4,6,6-pentamethyl-HCID 5360545Sodium

Product 1

HCID 145498982,2,4,4,6-Pentamethylhexahydropyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A sample of 27.4 grams 2,2,4,4,6-pentamethyl-2,3,4,5-tetrahydropyrimidine was dissolved in 50 grams of ethanol. To the ethanolic solution was added 6.9 grams of sodium metal at such a rate that a temperature of 70°-80° C. was maintained. After the addition was completed, the mixture was heated for one hour at 85°-95° C. The mixture was allowed to cool to room temperature and water added to the mixture. The organic layer was extracted with toluene, the toluene extract washed with water, dried, and the toluene removed, yielding 2,2,4,4,6-pentamethyl-hexahydroprimidine.

Workup

  1. temperaturewas maintained
  2. additionAfter the addition
  3. temperaturethe mixture was heated for one hour at 85°-95° C
  4. extractionThe organic layer was extracted with toluene
  5. extractionthe toluene extract
  6. washwashed with water
  7. customdried
  8. customthe toluene removed

Sources & evidence

ORD record
ord-8a5387481d5e476ba0741078aac592f2
Source dataset
uspto-grants-1983_09
Patent number
US04404302

Reaction notes

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