Methanol → HCID 15016793, compound

Participants

Reaction Steps

A mixture of 4,6-dichloro-5-nitro-2-ethylpyrimidine (0.5 g), Raney nickel (ca. 0.5 g) and MeOH (5 ml) was shaken in a hydrogen atmosphere at 1-2 p.s.i until reduction of the nitro group was complete. The mixture was filtered, evaporated to a black gum, taken up in a mixture of cyclopropylamine (5 ml, ca. 100 mmol) and isopropyl alcohol (5 ml) and heated in a bomb at 110° for 4 hours. The reaction mixture was then filtered, evaporated to dryness under reduced pressure and the pure product was isolated by preparative tlc using four 20×20 cm×1000μ silica gel GF plates developed with 1:1 EtOAc:hexanes; 315 mg of product was obtained. Yield: 64%. NMR (CDCl3, δ from TMS): 0.47(m) and 0.76(m) cyclopropyl methylenes, 1.24 (t, CH3), 2.69 (q, CH2CH3), 2.86 (m, CH), 3.47 (br s, NH2), 5.47 (br s, NH).

Provenance & Evidence