Methanol → 1,6-Dihydro-5(4H)-pyrimidinone O-methyloxime monohydrochloride

HRID 129815

Reaction equation

HRID 129815 reaction equation
O.[ClH:2].Cl.[NH2:4][CH2:5][C:6]([CH2:8][NH2:9])=O.[CH3:10][O:11][NH3+:12].[Cl-].[CH3:14]O>>[ClH:2].[CH3:10][O:11][N:12]=[C:6]1[CH2:8][NH:9][CH:14]=[N:4][CH2:5]1

Participants

4

Reactant 3

HCID 887MethanolHCID 11639O-methylhydroxylammonium chlorideHCID 190837391,3-Diaminopropan-2-one--hydrogen chloride--water (1/2/1)

Product 1

HCID 736056051,6-Dihydro-5(4H)-pyrimidinone O-methyloxime monohydrochlorideYield 36%

Procedure

1,3-Diaminoacetone dihydrochloride monohydrate (2.61 g, 14.6 mmol) was dissolved in refluxing methanol. To this solution o-methylhydroxylamine hydrochloride (2.43 g, 29.2 mmol) was added. After reflexing for 48 hours the solvents were evaporated. The crude product was dissolved in methanol and an excess of trimethylorthoformate was added to the reaction mixture which was heated to reflux. After 24 hours the solvent was removed in vacuo. crystallization from methanol/ethyl acetate afforded 850 mg (36%) of a light-brown crystalline material. Mp. 170.7° C.

Workup

  1. customthe solvents were evaporated
  2. dissolutionThe crude product was dissolved in methanol
  3. additionan excess of trimethylorthoformate was added to the reaction mixture which
  4. temperaturewas heated to reflux
  5. customAfter 24 hours the solvent was removed in vacuo
  6. customcrystallization from methanol/ethyl acetate

Sources & evidence

ORD record
ord-5a0b5e02eefc472db4304a28baf660fa
Source dataset
uspto-grants-1995_11
Patent number
US05470856

Linked notes

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