Sodium Chloride → 5-(benzyloxy)-2-(hydroxymethyl)-3-methyl-4(3H)-pyrimidinone

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Reaction Steps

5-(Benzyloxy)-2-(hydroxymethyl)-4(1H)-pyrimidinone (2.3 g) are dissolved in 20 ml of absolute methanol. The solution is treated with 4.24 g (40 mmol) of sodium carbonate and 10 ml of methyl iodide and stirred at room temperature for 4 days. Now, 400 ml of dichloromethane and 100 ml of saturated sodium chloride solution are added thereto, the organic phase is separated, dried over sodium sulphate and concentrated. The residue is chromatographed of 100 g of silica gel (0.063-0.2 mm). The two products are eluted in succession with dichloromethane/methanol (9:1 v/v). There are obtained 1.2 g of 5-(benzyloxy)-2-(hydroxymethyl)-3-methyl-4(3H)-pyrimidinone as white crystals from ether, m.p. 83°-84° C. 5-(Benzyloxy)-2-(hydroxymethyl)-1-methyl-4(1H)-pyrimidinone also forms white crystals from ether, m.p. 172°-173° C. 0.6 g is obtained.

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