Morpholine → 2-(Morpholinomethyl)pyrimidin-4-amine

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Reaction Steps

Following a procedure from J. Chem. Soc. Perkin. Trans. I, 1996, 2925, 2-chloromethyl-pyrimidin-4-ylamine (0.35 g, Eur. Pat. Appl. EP 61318 A2, 1982; Eur. Pat. Appl. 60094 A2, 1982) was dissolved in ethanol (10 mL) and triethylamine (0.51 mL) and morpholine (0.21 mL) were added. The mixture was heated to reflux for 48 hours and was then allowed to cool and evaporated in vacuo. The residue was dissolved in ethyl acetate and washed with 3N NaOH saturated with NaCl. The aqueous layer was subsequently re-extracted 5 times with ethyl acetate and the combined organic layers were dried over Na2SO4, filtered and evaporated. Flash chromatography (ethyl acetate/methanol 8:2) furnished the desired product 2-morpholin-4-ylmethyl-pyrimidin-4-ylamine as a light brown solid (0.23 g). 1H NMR (δ, DMSO-d6): 7.99 (d, 1H), 6.79 (br s, 2H), 6.28 (d, 1H), 3.56-3.53 (m, 4H, 3.36 (s, 2H), 2.46-2.43 (m, 4H). MS (ESI): 194.9 (MH+).

Provenance & Evidence