Butanedioic acid, 2-acetyl-, 1,4-diethyl ester → ethyl (2,6-dimethyl-3H-pyrimidin-4-on-5yl)acetate

HRID 1886056Notes

Reaction equation

HRID 1886056 reaction equation
CC[O-].[Na+].Cl.[C:6]([NH2:9])(=[NH:8])[CH3:7].[C:10]([CH:13]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:14](OCC)=[O:15])(=O)[CH3:11]>CCO>[CH3:7][C:6]1[NH:9][C:14](=[O:15])[C:13]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:10]([CH3:11])[N:8]=1

Participants

5

Reactant 3

HCID 66197Butanedioic acid, 2-acetyl-, 1,4-diethyl esterHCID 67170Acetamidine monohydrochlorideHCID 2723922Sodium ethoxide

Product 1

HCID 135459178ethyl (2,6-dimethyl-3H-pyrimidin-4-on-5yl)acetateYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of NaOEt (0.069 mol) in EtOH (prepared from 1.6 g of Na in 100 mL of EtOH), acetamidine hydrochloride (6.5 g, 0.069 mol), and diethyl 2-acetylsuccinate (15.0 g, 0.069 mol) was heated under reflux for 16 h. The mixture was concentrated, taken up in water (50 mL), and acidified with 2N HCl (12 mL). The aqueous mixture was extracted with CH2Cl2, and the extracts were dried (MgSO4) and concentrated. Trituration with ether gave 3.9 g (27%) of product as a white solid, mp 175°-177° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 h
  3. concentrationThe mixture was concentrated
  4. extractionThe aqueous mixture was extracted with CH2Cl2
  5. dry with materialthe extracts were dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cb767273792f4fc98ce74071b1580e31
Source dataset
uspto-grants-1992_09
Patent number
US05149699

Reaction notes

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