Water → HCID 178457185, compound

Participants

Reaction Conditions

Reaction Steps

TFA (0.75 ml) followed by water (0.1 ml) was added to a solution of 7-[(3aS,4R,6aR)-6-({[4-(5-tert-butyl-1H-1,3-benzodiazol-2-yl)butyl](propan-2-yl)amino}methyl)-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine in DCM (1.5 ml) and stirred at 50° C. for 2 hours. The reaction mixture was then evaporated in vacuo. MeOH (2 ml) was added to the residue and cooled to 0° C. This was basified with 7N ammonia in MeOH (3 ml) and then evaporated to dryness. The product was filtered though a short silica gel column, eluting with 7N ammonia in MeOH:DCM (5/95-1/9). This gave separation of two products plus a mixture of both. The mixed fractions were combined and purified on a prep. TLC plate, eluting twice with 7N ammonia in MeOH:DCM (1:9) to give a white solid (39 mg, 56%); MS (ESI+) for C30H43N7O2. m/z 534.48 [M+H]+; HPLC purity 98% (ret. time, 4.68 min); 1H NMR (250 MHz, MeOD) δ ppm 8.05 (1H, s), 7.48 (1H, s), 7.34-7.43 (1H, m), 7.22-7.31 (1H, m), 7.17 (1H, d, J=3.50 Hz), 6.59 (1H, d, J=3.50 Hz), 4.77-4.90 (1H, m), 4.29 (1H, dd, J=7.08, 5.86 Hz), 3.95 (1H, t, J=5.33 Hz), 3.09 (1H, s), 2.91 (2H, t, J=7.39 Hz), 2.64-2.78 (1H, m), 2.44-2.63 (3H, m), 2.14-2.41 (2H, m), 1.75-1.98 (2H, m), 1.48-1.68 (3H, m), 1.35 (9H, s), 1.04 (6H, dd, J=12.33, 6.55 Hz).

Provenance & Evidence