Sodium Hydroxide → 1,1-Dimethylethyl 4-[({2-[4-(methylsulfonyl)phenyl]-5-pyrimidinyl}oxy)methyl]-1-piperidinecarboxylate

Participants

Reaction Steps

The title compound (0.12 g, 31%) was prepared as a white solid from 1,1-dimethylethyl 4-({[2-(4-bromophenyl)-5-pyrimidinyl]oxy}methyl)-1-piperidinecarboxylate (0.385 g, 0.86 mmol), methanesulfinic acid sodium salt (0.16 g, 80%, 1.29 mmol), L-proline (20 mg, 0.17 mmol), Cul (17 mg, 0.09 mmol) and NaOH (7 mg, 0.17 mmol) in DMSO (5 mL) in a manner similar to Example 76, Step 3. 1H NMR (400 MHz, CD3OD): δ 8.60 (s, 2H), 8.57 (d, 2H, J=8.5 Hz), 8.03 (d, 2H, J=8.6 Hz), 4.20-4.10 (m, 2H), 4.08 (d, 2H, J=6.1 Hz), 3.15 (s, 3H), 2.90-2.75 (m, 2H), 2.15-2.00 (m, 1H), 1.90-1.80 (m, 2H), 1.46 (s, 9H), 1.40-1.25 (m, 2H); LRMS (ESI), m/z 448 (M+H).

Provenance & Evidence