4(1H)-Pyrimidinethione(9CI)

Step a General procedure: Scheme 6 A suspension of 0.508 g (4.44 mmol) of compound 17 and 0.338 g (4.44 mmol) of thiourea in 18 mL of ethanol was heated at 90C for 2 h. After this time, the reaction mixture was cooled to room temperature and concentrated. To the residue was added 30 mL of water, followed by 0.235 g (2.22 mmol) of sodium carbonate and the resulting solution was extracted with four 25 mL portions of methylene chloride. The combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated to afford 0.34 g (68%) of compound 18 as a dark-yellow solid: MS: Calcd. for C4H5N2S (MH+), m/z = 113.0; found 113.0. Retention time: 1.56 min.General procedure: To a solution of compound 1 (240 mg, 0.39mmol) in tetrahydrofuran (THF; 5ml) at 0 C were added triphenylphosphine (150 mg, 0.57 mmol), diethylazodicarboxylate (0.10ml, 0.55mmol) and benzo[d]oxazole-2-thiol (85 mg, 0.56ml) and stirred at 0 C for 1 h. The mixture was stirred at RT for 16 h. The mixture was diluted with 2N HCl (1ml)-MeOH (1ml) and then stirred at RT for 30 min and concentrated under reduced pressure. The resulting residue was dissolved by water and washed with diethyl ether. The mixture was added to NaHCO3 (150 mg), then extracted with ethyl acetate, washed with water, dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by preparative TLC (CHCl3/CH3OH/28 % aq NH4OH=20/1/0.1) toobtain the title compound as a colorless solid (147.6mg, 71%).

Molecular Weight:112.16
XLogP3:-0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:112.00951931
Monoisotopic Mass:112.00951931
Topological Polar Surface Area:56.5
Heavy Atom Count:7
Complexity:137
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes