Hydrochloric Acid → 1,2,6-trimethyl-3-ethyl-1,2,3,6,7,8,9,9a-octahydro-4-oxo-4H-pyrido(1,2-a)pyrimidine hydrochloride

HRID 1856481Notes

Reaction equation

HRID 1856481 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:5]2[C:6](=[O:10])[C:7]=1[CH2:8][CH3:9].[CH3:16]I.[BH4-].[Na+].[ClH:20]>C(O)C.O.CC(C)=O>[ClH:20].[CH3:16][N:3]1[CH:2]([CH3:1])[CH:7]([CH2:8][CH3:9])[C:6](=[O:10])[N:5]2[CH:11]([CH3:15])[CH2:12][CH2:13][CH2:14][CH:4]12

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 93406CH 150HCID 4311764Sodium borohydride

Product 1

HCID 205688671,2,6-trimethyl-3-ethyl-1,2,3,6,7,8,9,9a-octahydro-4-oxo-4H-pyrido(1,2-a)pyrimidine hydrochlorideYield 41%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

0.01 moles of 2,6-dimethyl-3-ethyl-4-oxo-4H-pyrido[1,2-a]pyrimidine are dissolved in 20 ml. of acetone, 0.03 moles of methyl iodide are added and the mixture is kept in a bomb tube at 150° C. for 24 hours. The solution is evaporated to dryness, the residue is dissolved in 15 ml. of methanol and a solution of 0.05 moles of sodium tetrahydroborate (III) in 10 ml. of water is added. After 4 hours the methanol is distilled off and the aqueous phase is extracted with three 20-ml. portions of chloroform. The organic phase is dried, evaporated and added to the oily substance obtained are 10 ml. of ethanol saturated with hydrochloric acid. 1,2,6-trimethyl-3-ethyl-1,2,3,6,7,8,9,9a-octahydro-4-oxo-4H-pyrido[1,2-a]pyrimidine hydrochloride is obtained, which crystallizes when triturated with ether. The product obtained after recrystallization from a mixture of acetone and ether sublimates over 206° C. Yield: 41%.

Workup

  1. customThe solution is evaporated to dryness
  2. dissolutionthe residue is dissolved in 15 ml
  3. distillationAfter 4 hours the methanol is distilled off
  4. extractionthe aqueous phase is extracted with three 20-ml
  5. customThe organic phase is dried
  6. customevaporated
  7. additionadded to the oily substance
  8. customobtained

Sources & evidence

ORD record
ord-fbbd07fd4dd348af9ae63b3f717387fc
Source dataset
uspto-grants-1980_08
Patent number
US04219649

Reaction notes

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