Aluminium lithium hydride → HCID 11683750, compound

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Reaction Steps

A solution of 4-[6-(6-carboxymethyl-2-methyl-pyridin-3-ylamino)-5-methoxy-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid isopropyl ester (TFA salt, 582 mg, 1.01 mmol) in 4 mL THF was cooled in an ice-water bath and lithium aluminum hydride (ca 190 mg, 5 mmol) was added in small portions. After 2 h, mixture was quenched with ice-water; solids were filtered off, and washed with THF. Filtrate was concentrated and purified by HPLC. Fractions containing product were partly concentrated and residue was extracted with 1 M NaOH and methylene chloride. Organic phases were dried over MgSO4, filtered, and concentrated to give 4-{6-[6-(2-hydroxy-ethyl)-2-methyl-pyridin-3-ylamino]-5-methoxy-pyrimidin-4-yloxy}-piperidine-1-carboxylic acid isopropyl ester as a white solid (85.0 mg, 19%). 1HNMR (CDCl3, 400 MHz) δ 1.25-1.27 (d, J=6.2 Hz, 6H), 1.80-1.86 (m, 2H), 2.00-2.05 (m, 2H), 2.72 (s, 3H), 3.16-3.19 (t, J=5.6 Hz, 2H), 3.38-3.44 (m, 2H), 3.76-3.82 (m, 2H), 3.96-3.99 (t, J=5.6 Hz, 2H), 4.00 (s, 3H), 4.91-4.97 (m, 1H), 5.37-5.41 (m, 1H), 5.30 (s, 1H), 5.37-5.41 (m, 1H), 7.03 (s, 1H), 7.36-7.38 (d, J=8.5 Hz, 1H), 8.13 (s, 1H), 8.85 (s, 1H). Exact mass calculated for C22H31N5O5 445.23. found 446.1 (MH+).

Provenance & Evidence