5-Pyrimidinol,2-(methylthio)-(6CI,7CI,8CI,9CI)

Step 1: 2-(Methylthio)pyrimidin-5-ol (CAS 75670-14-3, 3.5 g) was dissolved in DMF(68.6 ml) After addition of potassium carbonate (3.74 g) and ethyl chlorodifluoroacetate (4.29 g)the reaction mixture was stirred for 48h at 65C. The reaction mixture was diluted with water and extracted twice with AcOEt. The organic layers were washed with brine, dried over sodium sulphate, evaporated and purified by chromatography (silica gel, 0% to 40% EtOAc in n-heptane) to give 5-(difluoromethoxy)-2-(methylthio)pyrimidine (2.25 g) as a light yellow liquid. MS: mlz= 193.1 [M+H]?.Step 1: A suspension of Step 1: To a solution of Step 1 : To a solution of General procedure: A vial with a septum was charged with 4-hydroxybenzonitrile (78 mg, 0.656mmol), tert-butyl (2-chloropyridin-4-yl)carbamate(100 mg, 0.437 mmol), J009-PreCat (8.08 mg, 8.75 mumol), Cs2CO3 (285 mg, 0.875mmol) and a stir bar. The vessel was then evacuated under vacuum and refilledwith nitrogen three times. Toluene (1 mL) was injected under N2 andthe vial was sealed and heated at 100 oC for 24 h. The reactionmixture was then cooled to room temperature and diluted with EtOAc (5 mL). Themixture was then filtered through a pad of silica which was washed with EtOAc(2 x 5 mL). The filtrate was concentrated and purified on ISCO CombiFlash (4 gsilica gel column, 0-20% EtOAc in hexanes gradient)

Molecular Weight:142.18
XLogP3:0.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:142.02008399
Monoisotopic Mass:142.02008399
Topological Polar Surface Area:71.3
Heavy Atom Count:9
Complexity:83
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes