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

HRID 1288292ノート

反応式

HRID 1288292 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒3 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6875b44e8c4848cbbf145ad9586d55b2
出典データセット
uspto-grants-1976_10
特許番号
US03987160

反応ノート

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