Hydrochloric Acid → HCID 178433062, 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)) (350 mg, 1.44 mmol) and indoline (Aldrich Chemical Company) (350 mg, 2.94 mmol). The flask was purged with N2 and the mixture was heated to 180° C. for 1 h. The reaction was allowed to cool to room temperature and the crude material was purified by silica gel chromatography with 33% EtOAc/hexanes to give 250 mg (53% yield) of an off white solid. The free base (221 mg, 0.677 mmol) was dissolved in hot EtOAc (15 mL)and MeOH (2 mL) and anhydrous ethereal HCl (0.677 mL, of a 1.0 M soln, 0.677 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 239 mg (97% yield) of the title compound as a light yellow solid. Mp: >300° C. 1H NMR (DMSO-d6; 400 MHz): d 2.7 (s, 3), 4.87 (t, 2, J=8.2), 7.0 (s, 1), 7.17 (t, 1, J=7.5), 7.32 (t, 1, J=7.6), 7.58 (m, 3), 8.0 (d, 2, J=6.9), 8.53 (d, 1, J=3.3), 11.7 (br, 1), 14.55 (br, 1). MS m/z: 327.0 (M+1); 325 (M−1). Anal. Calcd for C21H18 N4. 1.0HCl. 1.25H2O: C, 65.45; H, 5.62; N, 14.54. Found: C, 65.62; H, 5.62; N, 14.49.

Provenance & Evidence