Aluminium lithium hydride → HCID 86629451, compound

Participants

Reaction Steps

LiAlH4 ((2.1 g, 54.7 mmol) was added portion wise to a 0° C. solution of ethyl 4-(tert-butylamino)-6-chloronicotinate (7 g, 27.3 mmol) in THF (100 mL). After 20 min, the reaction was quenched by the addition of water (2.1 mL), followed by 2 N aq NaOH (2 N, 2.1 ml. The resulting suspension was filtered and the filtrate was concentrated to afford (4-tert-butylamino-6-chloro-pyridin-3-yl)-methanol (5.0 g, 86.2% yield), which was used in next step without purification. 1H NMR (400 MHz, DMSO-d6): δ 7.73 (s, 1 H), 6.61 (s, 1 H), 5.87 (s, 1 H), 5.43 (t, J=5.2 Hz, 1 H), 4.38 (d, J=5.2 Hz, 2 H), 1.35 (s, 9 H).

Provenance & Evidence