2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-methanol

A solution of compound (3).(5g, 19.9 mmol) in THF (50 mL) was stirred at 29 °C undernitrogen atmosphere, tetrabutylammonium fluoride solution1.0M in THF (45 mL) was added to the mixture and heatedat 60 °C for 12 hours. Progress of the reaction was monitoredby TLC. After completion of the reaction, the resultingmixture was concentrated under vacuum and residue wasdissolved in 2-propanol (10 mL) at 50°C. The clear solutionwas cooled to 29°C, with slowly charged water (75 mL) andstirred for 4 hours. Precipitate was filtered and washed withwater, followed by being dried at 50°C under vacuum toobtain compound (4). Brown solid, Yield: 68percent, mp. 173-175 °C. 1H NMR (400 MHz, DMSO-d6): 1.64-1.65 (m, 2H, -CH2), 1.98-2.03 (m, 4H, CH2), 2.22-2.29 (m, 2H, CH2), 4.67(d, 2H, J=5.12 Hz, CH2OH), 4.87-4.89 (m, 1H, -NH-CH-), 5.52 (s, 1H, CH2OH), 6.55 (s, 1H, Ar-H), 8.82 (s, 1H, Ar-H).13C NMR (75.46 MHz, DMSO-d6): 152.3, 151.5, 150.9, 144.7, 118.21, 98.5, 56.4, 52.3, 30.7, 24.9. ESI-HRMS (m/z):Calcd. for C12H14ClN3O: 251.7129. Found: m/z 251.8001[M+].To a solution of 3-(2-chloro-4-(cyclopentylamino)pyrimidin-5-yl)prop-2-yn-l-ol (27 g) in tetrahydrofuran (270 mL) was added a solution of tetra butyl ammonium fluoride in tetrahydrofuran (1M , 268 mL) at 25-30 °C and stirred for 10 minutes at the same temperature. The reaction mass was then heated to 60 °C and stirred for 4 hours at the same temperature. The reaction mass was then cooled to 25-30 °C and evaporated under reduced pressure at 45 °C. Residue obtained from the evaporation was dissolved in 2-propanol (270 mL) and stirred for 15 minutes at 25-30 °C. Water (270 mL) was added to the above solution and again stirred for 30 minutes at 20 °C. Resulting solid compound was then filtered, washed with water (2 x 30 mL) followed by n- hexane (100 mL) and methyl tert-butyl ether (100 mL), dried for 16 hours at 50 °C to afford the title compound. (0160) Yield: 20 2 g; Purity by HPLC: 95 25 percent

Molecular Weight:251.71
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:251.0825398
Monoisotopic Mass:251.0825398
Topological Polar Surface Area:50.9
Heavy Atom Count:17
Complexity:273
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes