Benzamidine, hydrochloride → Ethyl 2-phenylpyrimidine-5-carboxylate

Reaction equation

[CH3:1][CH2:2][O:3][C:4](/[C:6](/[CH:11]=O)=[CH:7]/N(C)C)=[O:5].Cl.[C:14]([NH2:22])(=[NH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Na]>CCO>[C:15]1([C:14]2[N:22]=[CH:11][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:7][N:21]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Procedure

A solution of ethyl 3-N,N-dimethylamino-2-formylacrylate (4.0 g, 23 mmol) (Arnold, Coll. Czech. Chem. Commun. 26:3051, 1961), benzamidine hydrochloride (4.0 g, 26 mmol) and sodium (0.65 g, 28 mmol) in EtOH (40 mL) was heated at reflux for 1 h. The solution was filtered and concentrated and the residue partitioned between EtOAc and dilute HCl (10%). The organic layer was dried (Na2SO4), and concentrated to give ethyl 2-phenylpyrimidine-5-carboxylate (4.0 g, 75% yield); m.p. >220° C. (dec.).