Potassium Carbonate → HCID 178433158, compound

Participants

Reaction Conditions

Reaction Steps

To a 5-mL, Wheaton vial were added 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1(e)) (100 mg, 0.41 mmol) and ephedrine hydrochloride (Aldrich Chemical Company) (410 mg, 2.1 mmol), followed by addition of a solution of potassium carbonate (0.71 g, 5.1 mmol) in water (2.5 mL). The reaction mixture was stirred at 120° C. for 20 h, allowed to cool to room temperature and extracted with CH2Cl2. The organic layer was dried over Na2SO4, concentrated in vacuo to give a brown residue, which was purified by flash chromatography on silica gel with 1:1 EtOAc/hexanes as eluant to give 23 mg (15%) of the title compound as a tan solid. 1H NMR (DMSO-d6; 400 MHz): d 1.21 (d, 3, J=6.8), 2.42 (s, 3), 3.21 (s, 3), 4.91 (m, 1), 5.02 (m, 1), 5.87 (br s, 1), 6.69 (s, 1), 7.18-7.85 (m, 10), 10.73 (br s, 1). MS m/z: 373 (M+1), 371 (M−1).

Provenance & Evidence