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

HRID 129817

Reaction equation

HRID 129817 reaction equation
O.[ClH:2].Cl.[NH2:4][CH2:5][C:6]([CH2:8][NH2:9])=O.Cl.[CH3:11][CH:12]([O:14][NH2:15])[CH3:13].[CH3:16]O>>[ClH:2].[CH3:11][CH:12]([O:14][N:15]=[C:6]1[CH2:8][NH:9][CH:16]=[N:4][CH2:5]1)[CH3:13]

Participants

4

Reactant 3

HCID 887MethanolHCID 12696235O-(propan-2-yl)hydroxylamine hydrochlorideHCID 190837391,3-Diaminopropan-2-one--hydrogen chloride--water (1/2/1)

Product 1

HCID 736056031,6-Dihydro-5(4H)-pyrimidinone O-(1-methylethyl)oxime monohydrochlorideYield 47%

Procedure

1,3-Diaminoacetone dihydrochloride monohydrate (2.0 g, 11.2 mmol) was dissolved in refluxing methanol and O-(1-methylethyl)hydroxylamine hydrochloride (2.5 g, 22.4 mmol) was added. After refluxing for 48 hours the solvent was 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 1.00 g (47%) light-brown material. Mp. 170.0° C.

Workup

  1. additionwas added
  2. temperatureAfter refluxing for 48 hours the solvent
  3. customwas evaporated
  4. dissolutionThe crude product was dissolved in methanol
  5. additionan excess of trimethylorthoformate was added to the reaction mixture which
  6. temperaturewas heated to reflux
  7. customAfter 24 hours the solvent was removed in Vacuo
  8. customCrystallization from methanol/ethyl acetate

Sources & evidence

ORD record
ord-cb0d69c88875414e84b49d71fd746930
Source dataset
uspto-grants-1995_11
Patent number
US05470856

Linked notes

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