Ethyl cyanoacetate → 4-Amino-2-(2-ethoxyethyl)pyrimid-6-one

HRID 1288292Notes

Reaction equation

HRID 1288292 reaction equation
[O-][CH2:2]C.[Na+].[Na].[C:6]([CH2:8][C:9](OCC)=[O:10])#[N:7].Cl.[CH3:15][O:16][CH2:17][CH2:18][C:19]([NH2:21])=[NH:20]>C(O)C>[NH2:7][C:6]1[N:20]=[C:19]([CH2:18][CH2:17][O:16][CH2:15][CH3:2])[NH:21][C:9](=[O:10])[CH:8]=1

Participants

6

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 198475823-Methoxypropanimidamide--hydrogen chloride (1/1)

Product 1

HCID 1363546244-Amino-2-(2-ethoxyethyl)pyrimid-6-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To a solution of sodium ethoxide in ethanol, prepared from sodium (47.5 g.) and dry ethanol (675 ml.), was added, slowly with cooling and stirring, ethyl cyanoacetate (74 ml.), followed by a solution of 3-methoxypropionamidine hydrochloride (96 g.) in dry ethanol (173ml.). The mixture was stirred and heated under reflux for 40 hours, evaporated to dryness in vacuo, the residue triturated with water (67.5 ml.), acidified to pH 6 with concentrated hydrochloric acid, left to stand at 0° C. overnight and filtered. The aqueous filtrate was extracted continuously with ethyl acetate for 3 days and the extract dried and evaporated to dryness to give crude 4-amino-2-(2-ethoxyethyl)pyrimid-6-one (11.38 g.), m.p. 167°-170° C., sufficiently pure for use in the next stage. A sample was purified by chromatography on silica gel, followed by recrystallisation from ethanol, to give pure 4-amino-2-(2-ethoxyethyl)pyrimid-6-one, m.p. 191°-194° C.

Workup

  1. additionwas added
  2. temperatureslowly with cooling
  3. stirringThe mixture was stirred
  4. temperatureheated
  5. temperatureunder reflux for 40 hours
  6. customevaporated to dryness in vacuo
  7. customthe residue triturated with water (67.5 ml.)
  8. waitleft
  9. filtrationfiltered
  10. extractionThe aqueous filtrate was extracted continuously with ethyl acetate for 3 days
  11. customthe extract dried
  12. customevaporated to dryness
  13. customto give crude 4-amino-2-(2-ethoxyethyl)pyrimid-6-one (11.38 g.), m.p. 167°-170° C.
  14. customA sample was purified by chromatography on silica gel
  15. customfollowed by recrystallisation from ethanol

Sources & evidence

ORD record
ord-6875b44e8c4848cbbf145ad9586d55b2
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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