Hydrochloric Acid → HCID 59218357, compound

Participants

Reaction Steps

5-(5-(benzyloxy)pyridin-2-yl)-3-methyl-2-(methylthio)pyrimidin-4(3H)-one (2.5 g, 7.5 mmol) was suspended in 1,4-dioxane (40 ml) and aniline (6.4 ml, 70 mmol) and hydrochloric acid (concentrated, 0.10 ml, 3 mmol) were added. The flask was fitted with a reflux condenser and placed in a preheated oil bath (120 C) and stirred. After stirring at 120 C-130 C for almost 2 days, TLC shows mostly product formed. The reaction was cooled to room temperature, concentrated, and purified on silica gel (˜3 inches; DCM->100:1 DCM/MeOH->40:1->25:1->20:1->5:1 DCM/MeOH). Fractions with product were collected, concentrated, and put on high vac to afford the desired product 5-(5-(benzyloxy)pyridin-2-yl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one (1.5 g, 3.9 mmol, 53% yield). MS (ESI pos. ion) m/z: 385 (MH+). Calc'd exact mass for C23H20N4O2: 384.

Provenance & Evidence