Sodium hydride → HCID 11612683, compound

Participants

Reaction Steps

N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-3-[2-(methylamino)ethoxy]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (prepared as described in Example 24/50 mg, 0.12 mmol) was dissolved in DMA (1 ml) and 4-bromobutyryl chloride (14 μl, 0.12 mmol) was added drop-wise at −15° C. After 1 hour at room temperature, sodium hydride (60%, 29 mg) was added to the mixture and stirring was continued for 3 hours. The reaction was quenched with water and the crude product was purified by preparative HPLC (column beta-basic, Hypercil 5 μm, 21×100 mm) eluting with a mixture of water and acetonitrile containing 2g/l of ammonium carbonate (gradient) to give the title compound (5 mg, 9%); NMR Spectrum: 1.90-1.95 (m, 2H), 2.25 (t, 2H), 3.47 (t, 2H), 3.68 (br s, 2H), 4.39 (br s, 2H), 5.28 (s, 2H), 7.25 (d, 1H), 7.36 (t, 1H), 7.57 (d, 1H), 7.80-7.89 (m, 2H), 8.16 (br s, 2H), 8.32 (s, 1H), 8.59 (d, 1H); Mass Spectrum: 480 (MH+).

Provenance & Evidence