2-CHLORO-4-METHYL-6-METHYLSULFANYL-PYRIMIDINE

To a stirred solution of 2. 4-dichloro--6-methylpyrimidine 1 (200 tug, 1 22 mmol) under argon atmosphere in TNT (10 mL.) was added sodium methanethiolate (103 mg, 1.47 rumol in 4 mL of water) at —10 °C and stirred for 2 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was diluted with water (20 mL) and extracted. with EtO.Ac (2 x 30 niL). The combined organic extracts were dried over sod jum sulfate. filtered and concentrated in vacio to obtain the crude prodtwt. The crude product was purified through silica gel column chromatography using 3percent EtOAc hexanes to afford compound 166 (1 30 mg, 61percent) as a white solid. TLC: 5percent EtOAc/ Toluene (R, ’: 08) ‘H—NMR (DMSO—d6, 400 MHz): 67.38 (s, 11-1;. 2.53 (s. 311). 2.37 (5, 311).To a stirred solution of 2, 4-dichloro-6-methylpyrimidine 1 (200 mg, 1.22 mmol) under argon atmosphere in THF (10 mL) was added sodium methanethiolate (103 mg, 1.47 mmol in 4 mL of water) at -10 °C and stirred for 2 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2 x 30 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 3percent EtOAc/ hexanes to afford compound 54 (130 mg, 61percent) as white solid. TLC: 5percent EtOAc/ Toluene (Rf. 0.8); 1H-NMR (DIVISOR, 400 MHz): δ 7.38 (s, 1H), 2.53 (s, 3H), 2.37 (s, 3H).Step 1: Synthesis of2-chloro-4-methyl-6-(methylthio)pyrimidine. (0274) 2, 4-Dichloro-6-methylpyrimidine (20.0 g, 0.123 mol) was dissolved in THF (200 niL). MeSNa (20percent aq, 43g, 0.129 mol) was added dropwise at -5 °C, and the resulting mixture was stirred overnight at room temperature. HTo a stirred solution of 2, 4-Dichloro-6-methylpyrimidine [0086j (5 g, 30.674 mmol) in tetrahydrofuran (50 mL) was added sodium thiomethoxide (2.14 g, 30.67 mmol) in portions at -10 °C under nitrogen. The mixture was stirred at -10 °C for 3 h. The solid precipitate was filtered, washed with methanol (20 mL) and dried under vacuum to afford 2-chloro-4-methyl-6-(methylthio)pyrimidine [0099j as an yellow solid (5 g). MS(M+i)=i75.

Molecular Weight:174.65
XLogP3:2.4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:174.0018471
Monoisotopic Mass:174.0018471
Topological Polar Surface Area:51.1
Heavy Atom Count:10
Complexity:112
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes