Acetamidine monohydrochloride → 3-(4-Hydroxy-2,6-dimethyl-pyrimidin-5-yl)-propionic acid ethyl ester

HRID 1886059Notes

Reaction equation

HRID 1886059 reaction equation
CC[O-].[Na+].Cl.[C:6]([NH2:9])(=[NH:8])[CH3:7].[C:10]([CH:13]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:14](OCC)=[O:15])(=O)[CH3:11]>CCO>[CH3:7][C:6]1[NH:9][C:14](=[O:15])[C:13]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:10]([CH3:11])[N:8]=1

Participants

5

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 73915Diethyl 2-acetylglutarateHCID 2723922Sodium ethoxide

Product 1

HCID 1359679873-(4-Hydroxy-2,6-dimethyl-pyrimidin-5-yl)-propionic acid ethyl esterYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of NaOEt (0.069 mol) in EtOH (prepared from 1.6 g of Na and 35 mL of EtOH), acetamidine hydrochloride (3.3 g, 0.035 mol), and diethyl acetylglutarate (8.0 g, 0.035 mol) was heated under reflux for 22 h. The mixture was concentrated, taken up in water, acidified to pH 4 with conc. HCl, and extracted with EtOAc. The extracts were washed with brine, dried (MgSO4), and concentrated. Trituration with hexane gave 4.0 g (51%) of product as a white solid. An analytical sample was crystallized from ether/hexane, mp 114°-116° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 22 h
  3. concentrationThe mixture was concentrated
  4. extractionextracted with EtOAc
  5. washThe extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2b9a40c7f0cb43568f875650261b45d5
Source dataset
uspto-grants-1992_09
Patent number
US05149699

Reaction notes

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