4-Chloro-6-methyl-1H-pyrazolo[3,4-d]pyrimidine

6-Methyl-1, 5-dihydro-pyrazolo[3, 4-d]pyrimidin-4-one (134 mg, 0.89 mmol.) was taken into thionyl chloride (3 mL) followed by addition of DMF (0.2 mL) and the mixture was brought to reflux over 30 minutes. The resulting solution was concentrated and the residue partitioned with ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was washed with brine then dried over anhydrous sodium sulfate, filtered and concentrated to afford a yellow oil.To a stirred solution of 4-Chloro-6-methyl-1 H-pyrazolo[3, 4-d]pyrimidine (2.0 g, 11 .51 mmol) in DMF (9.2 ml) under argon at 0C was added 2, 2, 2-trifluoroethyl trifluoromethanesulfonate (2.5 ml, 17 mmol) followed by potassium carbonate (3.2 g, 23 mmol). The mixture was stirred for 16h at room temperature. The suspension was filtrated through celite and evaporated off. The orange residue was purified by flash chromatography (Biotage Isolera: 100 g KP-Sil 0-60%hexane/ethyl acetate gradient) to give the desired product 13 (1.05 g, 29%) and 4-chloro-6- methyl-i -(2, 2, 2-trifluoroethyl)-1 H-pyrazolo[3, 4-d]pyrimidine (1.34 g, 40%).LC-MS (method 2): Rt = 0.74 mm; MS (ESIpos): mz = 251 [M+H]1HNMR (400 MHz, CHLOROFORM-d) 6 [ppm]: 1.267 (0.54), 1.594 (6.29), 2.054 (1.03), 2.687(3.48), 2.705 (0.45), 2.815 (16.00), 4.962 (0.82), 4.983 (1.05), 5.005 (0.84), 5.021 (1.12), 5.040(3.28), 5.061 (3.25), 5.081 (1.05), 8.176 (0.83), 8.233 (3.65).

Molecular Weight:168.58
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:168.0202739
Monoisotopic Mass:168.0202739
Topological Polar Surface Area:54.5
Heavy Atom Count:11
Complexity:154
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes