Tetrahydrofuran → HCID 86661299, compound

Participants

Reaction Steps

LiAlH4 (5.5 mL, 5.5 mmol, 1 M in THF) was added to a THF (30 mL) solution of methyl 2-(3-(3-fluorobenzyl)ureido)-5-isopropylthiazole-4-carboxylate (780 mg, 2.22 mmol) at 0 C. Upon completion of the reaction Na2SO4x10H2O (1.5 g, 4.5 mmol) was added carefully. The suspension was stirred for a day at ambient temperature which was followed by the addition of NaHSO4 (0.5 g, 4.5 mmol) and MeOH (5 mL). The mixture extracted with CH2Cl2, washed with dilute HCl, dried and evaporated to afford 1-(3-fluorobenzyl)-3-(4-(hydroxymethyl)-5-isopropylthiazol-2-yl)urea. 1H NMR (400 MHz, CDCl3): δ 7.70 (s, 1H, br), 7.24 (m, 1H), 7.05 (d, 1H), 6.99 (d, 1H), 6.92 (td, 1H), 4.55 (s, 2H), 4.41 (d, 2H), 3.20 (m, 1H), 1.27 (d, 6H). MS (ES+): M/Z 324 (M+H)+.

Provenance & Evidence