Dichloromethane → HCID 178433084, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-chloro-2-methyl-6-phenyl-pyrrolo[3,2-d]pyrimidine (Example 1(e)) (83.8 mg, 0.34 mmol) and 3,5-dimethylpiperidine (cis/trans, Aldrich Chemical Company) (250 μL, 1.72 mmol) was added a solution of K2CO3 (0.19 g, 1.36 mmol) in H2O (2.0 mL). This mixture was stirred at 140° C. in a closed-capped Wheaton vial for 2.0 h. After cooling, CH2Cl2 (10 mL) and H2O (10 mL) were added. The organic solution was removed and the aqueous solution washed with CH2Cl2 (10 mL). The combined organic solutions were washed with saturated NaCl (15 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (3% MeOH:CHCl3 on silica gel) and then recrystallized from MeOH/CH2Cl2 to give 85 mg (78%) as a beige colored solid. This material was recrystallized from hot MeOH/CH2Cl2 to give 54 mg (50%) of the title compound as a 95:5 mixture of isomers as colorless crystals. Mp: 225.5-227° C. MS m/z: 321 (M+1). 1H NMR (DMSO-d6; 400 MHz) (for major isomer): δ 0.90 (m, 2), 0.91 (d, 6, J=6.5), 1.73 (m, 2), 2.40 (s, 3), 2.42 (br s, 2), 4.42 (br d, 1, J=8.2), 6.74 (s, 1), 7.40 (m, 1), 7.49 (br s, 2), 7.89 (d, 2, J=7.4), 11.06 (s, 1). Anal. Calcd for C20H24N4: C, 75.00; H, 7.50; N, 17.50. Found: C, 74.87; H, 7.56; N, 17.38.

Provenance & Evidence