Hydrochloric Acid → HCID 178433098, compound

Participants

Reaction Conditions

Reaction Steps

To an oven-dried, 50-mL, round-bottomed flask was added 2-methyl-6-phenyl-4-piperazinylpyrrolo[3,2-d]pyrimidine (Example 26) (400 mg, 1.36 mmol) was suspended in anhydrous THF (20 mL) and Et3N (0.4 mL, 2.8 mmol) was added. The mixture was cooled to 0° C. and methanesulfonyl chloride (Aldrich Chemical Company) (0.12 mL, 1.5 mmol) was added dropwise and allowed to warm to room temperature over 30 min. EtOAc (50 mL) was added to the mixture which was extracted with saturated NaHCO3 (3×50 mL). The organic layer was washed with saturated NaCl (75 mL), dried over MgSO4, filtered and evaporated in vacuo to give 450 mg (89% yield) as a light yellow solid. The free base (440 mg, 1.2 mmol) was dissolved in hot EtOAc (20 mL) and anhydrous ethereal HCl (1.18 mL, of a 1.0 M soln, 1.18 mmol) was added dropwise. The mixture was stirred for 2 h and allowed to cool to room temperature. The resulting solid was filtered and dried under high vacuum to give 460 mg (95.6% yield) of the title compound as a light yellow solid. Mp: 280-282° C. 1H NMR (DMSO-d6; 400 MHz); d 2.54 (s, 3), 2.88 (s, 3), 3.29 (s, 4), 4.13 (t, 4, J=4.62), 6.9 (s, 1), 7.51 (m, 3), 7.94 (d, 2, J=6.85). MS ml/z: 372 (M+1); 370 (M−1). Anal. Calcd for C18 H21N5O2S.HCl.H2O′.: C, 50.46; H, 5.70; N, 16.35; Cl, 8.41. Found: C, 50.71; H, 5.60; N, 16.22; Cl, 8.45.

Provenance & Evidence