Dichloromethane → 4-((4-Aminonaphthalen-1-yloxy)methyl)pyrimidin-2-amine

Participants

Reaction Steps

A solution of 4-((4-nitronaphthalen-1-yloxy)methyl)pyrimidin-2-amine (32) (1.10 g, 3.71 mmol) in a DCM (50 mL) and AcOH (40 mL) was passed through a Thales H-cube at 1.0 mL·min−1 (full hydrogen mode, 55 mm 10% Pt/C, 40° C.). LC-MS analysis of the solution showed mainly starting material and ca. 20% product. The DCM was evaporated and the solution re-subjected to the above reducing conditions at RT. Analysis showed ca. 70% product together with ca. 20% over reduction and ca. 10% starting material. The volatiles were evaporated to give crude 4-((4-aminonaphthalen-1-yloxy)methyl)pyrimidin-2-amine (33) as a purple solid (0.90 g, 64% yield): m/z 267 (M+H)+ (ES+).

Provenance & Evidence