5-Ethylthiomethyl- und 5-Ethylsulfonylmethylpyrimidine

Synthesis of Dihydrobenzo[b]pyrimido[4,5-e][1,4]Thiazepines; Derivatives of a Novel Ring System

“…25 The reaction of (1) with formaldehyde in aqueous 5% NaOH solution at room temperature gave 5-(hydroxymethyl)-6-methylpyrimidine-2,4(1H,3H)-dione (2) 26 which was subsequently converted with a little modification into 2,4-dichloro-5-(chloromethyl)-6-methylpyrimidine (3) in boiling POCl 3 and N(i-Pr) 2 Et. 27 The compound (3) was treated with o-aminothiophenol (4) as a binucleophile at -15 ºC in CHCl 3 . (Scheme 1) The evidence which confirms both 4-Cl and the chloromethyl group on the pyrimidine core were substituted by sulfur and amino groups of o-aminothiophenol, respectively, and formation of compound ( 5) can be deduced from previously published methods.…”