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Step B: 5-Iodo-2,6-dimethylpyrimidin-4-ol (4.6 g, 18.4 mmol) was combined with phosphorus oxychloride (15 mL). The mixture was stirred at 110 C. for 2 h, then the solvent was removed under vacuum. The residue was dissolved in CH2Cl2 and washed with an aqueous saturated NaHCO3 solution and brine. The organic layer was concentrated and purified by silica gel column chromatography (0-10% EtOAc in CH2Cl2) to give the title compound (3.86 g, 78%) as colorless oil that solidified on standing. MS m/z 269.2 [M+H]+.
33.8 g (62%)
With trichlorophosphate; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; toluene;
Step 2 4-Chloro-2,6-dimethyl-5-iodopyrimidine A mixture of <strong>[83410-37-1]2,6-dimethyl-5-iodo-4-hydroxypyrimidine</strong> (24.5 g, 0.098 mol), phosphorus oxychloride (30.0 g, 0.196 mol) and toluene (200 mL) was heated under reflux for 1 h. The mixture was concentrated and ice water (100 mL) was added. The pH was adjusted to 5 with 2.5N NaOH and the mixture was extracted with CH2 Cl2. The combined extracts were washed with brine, dried MgSO4), and concentrated to give 24.6 g of a brown solid. The crude product was combined with 26.0 g of similarly prepared material and filtered through a short column of silica gel eluted with CH2 Cl2 to give 33.8 g (62%) of product as a yellow solid. An analytical sample was recrystallized from hexane/CH2 Cl2, mp 62-64 C. 1 H NMR (CDCl3) delta2.61 (s, 3H), 2.73 (s, 2H). Anal. calcd for C6 H6 ClIN2: C, 26.84; H, 2.26; N, 10.44; Found: C, 27.04; H, 2.15; N, 10.14.
4-Chloro-5-iodo-2,6-dimethylpyrimidine (9); <n="32"/>[0096] To a solution of 1 g (4 mmol, leq.) of <strong>[83410-37-1]5-iodo-2,6-dimethylpyrimidin-4-ol</strong> (8) in 10 mL of toluene was added 1.21 g (8 mmol, 2 eq.) of POCl3 and the mixture was heated at reflux for 1 h. The mixture was concentrated and ice water was added. The pH was adjusted to 5 with 2.5 N NaOH and extracted with CH2Cl2. The combined extracts were washed with brine, dried (Na2SO4) and the solvent removed in vacuo. Then the crude product was purified by flash chromatography to provide 4-chloro-5-iodo-2,6-dimethylpyrimidine (9).
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