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

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

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 either gave 3.9 g (27%) of product as a white solid, mp 175°177° C.