Pyrrolidine → HCID 66780214, compound

Participants

Reaction Steps

To a 20 mL I-CHEM reaction vial was added a solution of 5-(bromomethyl)-4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (188 mg, 0.400 mmol) in tetrahydrofuran (THF) (4002 μL). The solution was then treated with pyrrolidine (331 μL, 4.00 mmol) and the resulting reaction mixture was allowed to stir at room temperature and was found to have completely converted to the desired material by LCMS in less than 5 minutes. Reaction mixture was placed under a nitrogen stream and warmed to 50° C. to concentrate the reaction to a residue. The residue was then re-dissolved in dichloromethane (DCM) (750 μL) and injected onto a 10 g SNAP silica cartridge for purification [eluting with a gradient: 0-95% THF (1% methanol (MeOH)) into DCM, over 30 column volumes]. Fractions containing the desired material were pooled and concentrated to afford a residue which was subsequently triturated with ethyl acetate and hexanes to afford pure 4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl)-5-(1-pyrrolidinylmethyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (38 mg, 0.082 mmol, 20.44% yield). LCMS Theoretical m/z MH+=460.99 Found: 461.2; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.47 (br. s., 4H) 2.37 (br. s., 4H) 2.41 (s, 3H) 3.46-3.52 (m, 4H) 3.52 (s, 2H) 3.62-3.74 (m, 4H) 5.66 (s, 2H) 6.45 (d, J=7.83 Hz, 1H) 7.11 (t, J=8.21 Hz, 1H) 7.33 (d, J=7.33 Hz, 1H).

Provenance & Evidence