Diethyl 2-acetylglutarate → Ethyl 3-(6-Methyl-2-methoxymethyl-3H-pyrimidin-4-on-5-yl)propionate

HRID 129007Notes

Reaction equation

HRID 129007 reaction equation
CC[O-].[Na+].Cl.[CH3:6][O:7][CH2:8][C:9]([NH2:11])=[NH:10].[C:12]([CH:15]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:16](OCC)=[O:17])(=O)[CH3:13]>CCO>[CH3:13][C:12]1[N:11]=[C:9]([CH2:8][O:7][CH3:6])[NH:10][C:16](=[O:17])[C:15]=1[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 3

HCID 73915Diethyl 2-acetylglutarateHCID 2723922Sodium ethoxideHCID 135486022-Methoxyethanimidamide hydrochloride

Product 1

HCID 136067006Ethyl 3-(6-Methyl-2-methoxymethyl-3H-pyrimidin-4-on-5-yl)propionateYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of NaOEt (0.088 mol) in EtOH (prepared from 2.0 g of Na and 70 mL of EtOH), methoxyacetamidine hydrochloride (5.4 g, 0.044 mol), and diethyl acetylglutarate (10.0 g, 0.044 mol) was heated under reflux for 24 h. The mixture was concentrated, taken up in water, acidified to pH 4 with conc. HCl, and extracted with CH2Cl2. The extracts were washed with brine, dried (MgSO4), and concentrated. Trituration with ether gave 4.6 g (42%) of product as an off-white solid, mp 87°-90° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 h
  3. concentrationThe mixture was concentrated
  4. extractionextracted with CH2Cl2
  5. washThe extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2e0daf3a169947c4b577469e4a661227
Source dataset
uspto-grants-1995_11
Patent number
US05466692

Reaction notes

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