Toluene → HCID 18511070, compound

Participants

Reaction Steps

A solution of 2-methyl-4-chloro-6-phenyl pyrrolo[3,2-d]pyrimidine (1.0 g, 4.1 mmol, Example 1e) and 2-hydroxymethyl piperidine (Aldrich Chemical Company) (0.49 g, 4.2 mmol) in N-methyl morpholine (10 mL) was heated at 110° C. for 12 h. The solvent was concentrated in vacuo and the residue was mixed with POCl3 (5 mL, 54 mmol) and toluene (20 mL). The mixture was heated at reflux for 6.5 h before it was concentrated in vacuo. The residue was taken up in CH2Cl2 (50 mL)-H2O (50 mL) and the pH of the aqueous phase was adjusted to pH˜8 with NaOH solution (2 N). The organic phase was separated and the aqueous phase was extracted with CH2Cl2 (3×). The combinbed organic phase was dried over Na2SO4, concentrated in vacuo, and the resulting residue was purified by flash chromatography on silica gel (MeOH in CH2Cl2, 1-15%). The free base was treated with ethereal HCl to give the title compound as the HCl salt (0.18 g, 14%). Mp: >280° C. 1H NMR (DMSO-d6; 500 MHz): d 1.58-1.66 (m, 3), 1, 85-1.91 (m, 2), 2.05 (d, 1, J=10), 2.55 (s, 3), 3.43 (t, 1, J=10), 4.22-4.25 (m, 2), 4.77 (t, 1, J=14), 4.86(d, 1, J=13), 7.10 (s, 1), 7.49-7.57 (m, 3), 8.02 (d, 2, J=8). MS m/z: 305 (M+1). Anal. Calcd for C19H20N4.2HCl.H2O: C, 57.72; H, 6.12; N, 14.18; Cl, 17.95. Found: C, 57.69; H, 6.24; N, 14.02; Cl, 17.79.

Provenance & Evidence