2-Acetylbutyrolactone → 2,3-Diamino-5-(2-hydroxyethyl)-6-methylpyrimidin-4(3H)-one

HRID 482967Notes

Reaction equation

HRID 482967 reaction equation
C(=O)(O)O.[NH2:5][NH:6][C:7]([NH2:9])=[NH:8].[C:10]([CH:13]1[CH2:18][CH2:17][O:16][C:14]1=[O:15])(=O)[CH3:11]>C(O)CCC>[NH2:8][C:7]1[N:6]([NH2:5])[C:14](=[O:15])[C:13]([CH2:18][CH2:17][OH:16])=[C:10]([CH3:11])[N:9]=1

Participants

4

Reactant 2

HCID 106012-AcetylbutyrolactoneHCID 178513185HCID 178513185, compound

Product 1

HCID 133817382,3-Diamino-5-(2-hydroxyethyl)-6-methylpyrimidin-4(3H)-oneYield 65.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 13.6 g of aminoguanidine bicarbonate and 12.8 g of 2-acetyl butyrolactone in 80 ml of n-butanol was heated at reflux until a clear solution was obtained. This solution was cooled, evaporated to dryness in vacuo and the residue was triturated with 200 ml of a 50/50 ether-chloroform mixture, giving 12 g of the desired intermediate, mp 126°-135° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux until a clear solution
  3. customwas obtained
  4. temperatureThis solution was cooled
  5. customevaporated to dryness in vacuo
  6. customthe residue was triturated with 200 ml of a 50/50 ether-chloroform mixture

Sources & evidence

ORD record
ord-87799a5586e54577b601993e30d2f3cd
Source dataset
uspto-grants-1986_03
Patent number
US04577018

Reaction notes

Loading…