Sodium borohydride → HCID 22636813, compound

Participants

Reaction Steps

Sodium borohydride (45 mg; 1.2 mmol) is added to (E)-3-[1-[4-(2,4-diamino-pyrimidin-5-ylmethyl)-6-ethoxy-4′-methoxy-biphenyl-2-yloxymethyl]-cyclopropyl]-acrylonitrile (220 mg; 0.467 mmol) in isopropanol (25 ml) and the mixture is stirred for 19 hours under reflux. The reaction mixture is concentrated, the residue is stirred with water (15 ml), the mixture is adjusted to pH 2 with 1 N aqueous hydrochloric acid and back to pH 9 with conc. NH4OH and filtered with suction and the residue is dried under a high vacuum. The crude product is chromatographed over silica gel (20 g) with methylene chloride/methanol/NH4OH conc. (19/1/0.05). The pure fractions are concentrated together and the residue is stirred with diethyl ether, filtered off with suction and dried under a high vacuum. 75 mg (34%) 3-{1-[4-(2,4-diamino-pyrimidin-5-ylmethyl)-6-ethoxy-4′-methoxy-biphenyl-2-yloxymethyl]-cyclopropyl}-propionitrile are obtained as a colourless powder.

Provenance & Evidence