Hydrochloric Acid → HCID 178433094, compound

Participants

Reaction Conditions

Reaction Steps

To an oven-dried, 50-mL, round-bottomed flask was added 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1(e)) (500 mg, 2.05 mmol) and the 1-(2-furoyl)piperazine (Avocado Chemical Company) (810 mg, 4.10 mmol). The flask was purged with N2 and the mixture was heated to 180° C. for 30 min. The reaction was allowed to cool to room temperature and the crude material was purified by flash chromatography on silica gel with 50% EtOAc/CHCl3 as eluant to give 500 mg (63% yield) of an off white solid. The free base (200 mg, 0.52 mmol) was dissolved in hot EtOAc (10 mL) and anhydrous ethereal HCl (0.52 mL, of a 1.0 M soln, 0.52 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 205 mg (96% yield) of the title compound as a light yellow solid. Mp: 192-193° C. 1H NMR (DMSO-d6; 400 MHz): d 2.54 (s, 3), 3.89 (br s, 4), 4.17 (t, 4, J=4.3), 6.62 (q, 1, J=1.7), 6.9 (s, 1), 7.05 (d, 1, J=3.4), 7.4 (m, 3), 7.85 (s, 1), 7.93 (d, 2, J=6.92). MS m/z: 388 (M+1). Anal. Calcd for C22H21N5O2.HCl.H2O: C, 59.79; H, 5.47; N, 15.85; O, 10.86; Cl, 8.02. Found: C, 59.99; H, 5.33; N, 15.79; Cl, 8.06.

Provenance & Evidence