6-CHLOROTHYMINE

A stirred suspension of 5-methylbarbituric acid (5{1, 2}) (9.40 g, 0.66 mol) and benzyltrielthylammonium chloride (BTAC) (30.14 g, 0.13 mol) in phosphorus oxychloride (POClGeneral procedure: A suspension of 6{w, x} and N, O-bis-(trimethylsilyl)-acetamide (BSA) in anhydrous dichloromethane was stirred at room temperature for 2 h under nitrogen atmosphere. To the resulting solution, tetrabutylammonium iodide (TBAI) in one portion at room temperature, and the mixture was immediately cooled to 0 C. 7{y} was slowly added to the reaction mixture at 0 C, and the mixture was stirred for an additional 2 h in an ice bath. The reaction mixture was poured into saturated sodium bicarbonate solution and ice, and stirred for 30 min. The organic phase was separated and the aqueous phase was extracted with dichloromethane. The combined organic phase was washed with brine, dried over anhydrous magnesium sulfate and evaporated to dryness in vacuo. The residue was purified by flash column chromatography on silica gel with the corresponding eluent.A stirred solution of crude 2, 4, 6-trichloro-5-methylpyrimidine a4 (8.00 g, 40.8 mmol) in a 10% aqueous solution of NaOH (75 mL) was heated to reflux for 1.5 h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was acidified to pH 2 with a 2 N aqueous solution of HCI, filtered and dried under vacuum to afford 4.8 g of 6- chloro-5-methylpyrimidine-2, 4(1 H, 3H)-dione a5 as a white solid, which was used in next step without any further purification. Yield (crude): 21 % 1H NMR (400 MHz, DMSO -cfe) d 11.78 (s, 1 H), 1 1.29 (s, 1 H), 1.80 (s, 3H).

Molecular Weight:160.56
XLogP3:0.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:160.0039551
Monoisotopic Mass:160.0039551
Topological Polar Surface Area:58.2
Heavy Atom Count:10
Complexity:234
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes