Methanol → 1,6-Dihydro-5(4H)-pyrimidinone O-(2-propynyl)oxime monohydrochloride

HRID 129816

Reaction equation

HRID 129816 reaction equation
O.[ClH:2].Cl.[NH2:4][CH2:5][C:6]([CH2:8][NH2:9])=O.Cl.[CH2:11]([O:14][NH2:15])[C:12]#[CH:13].[CH3:16]O>>[ClH:2].[CH2:11]([O:14][N:15]=[C:6]1[CH2:8][NH:9][CH:16]=[N:4][CH2:5]1)[C:12]#[CH:13]

Participants

4

Reactant 3

HCID 887MethanolHCID 13502403O-(prop-2-yn-1-yl)hydroxylamine hydrochlorideHCID 190837391,3-Diaminopropan-2-one--hydrogen chloride--water (1/2/1)

Product 1

HCID 736056041,6-Dihydro-5(4H)-pyrimidinone O-(2-propynyl)oxime monohydrochlorideYield 36%

Procedure

1,3-diaminoacetone dihydrochloride monohydrate (1.10 g, 6.14 mmol) was dissolved in refluxing methanol and O-(2-propynyl)hydroxylamine hydrochloride (0.730 g, 6.75 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 and heated to reflux. After 24 hours the solvent was removed in vacuo. Crystallization from methanol/ethyl acetate afforded 410 mg (36%) of light-brown material. Mp. 205.0° 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
  6. temperatureheated to reflux
  7. customAfter 24 hours the solvent was removed in vacuo
  8. customCrystallization from methanol/ethyl acetate

Sources & evidence

ORD record
ord-98086c9c03a94f4bbefe958470294dc0
Source dataset
uspto-grants-1995_11
Patent number
US05470856

Linked notes

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