Synthesis of site specifically deuterated primaquines II. N-alkyl deuterated primaquines

Two site specifically deuterated primaquines were prepared. 4′,4′‐Dideutero primaquine 3 was obtained from the corresponding dideutero alcohol which was prepared by the low temperature reduction of the ester compound 4 with lithium aluminium deuteride. 1′‐Deutero primaquine r was prepared by the reductive alkylation of 6‐methoxy‐8‐aminoquinoline with N‐(2‐oxopentyl)‐phthalimide in the presence of sodium cyanoborodeuteride followed by removal of protective phthalimide group.