5-Chloro-2(1H)-pyrimidinone → 1(4-Chlorophenylsulfinyl)methyl-5-chloropyrimidin-2-one

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Reaction Steps

Potassium tert-butoxide (4 mmol) in DMF (10 ml) was added to a solution of 5-chloropyrimidin-2-one (4 mmol) in DMF (40 ml). The mixture was stirred at room temperature for 10 min before 1-bromomethylsulfinyl-4-chlorobenzene (see Preparation 5) (4 mmol) was added. The resultant mixture was stirred at 60° C. for 2 days, the solvent distilled off at reduced pressure, the residue triturated with water, the insoluble material dried and washed with a little chloroform before recrystallization from DMSO; the crystalline material was also washed with a little methanol and finally with water; yield 0.30 g (25%), m.p. 262° C. (Found: C43.63; H2.68. Calc. for C11H8Cl2N2O2S: C43.59; H2.67)1H NMR (DMSO-d6): δ 5.12 (CH2), 7.60 (Ph, b.s.), 8.19 and 8.62 (H-4, H-6, d, J 4 Hz). IR (KBr): 1660 (CO), 1060 cm-1 (SO) MS (70 eV; m/e (rel int. %): 302 (0.5, M), 159 (6), 145 (33), 143 (100).

Provenance & Evidence