Boron tribromide → HCID 136121098, compound

Participants

Reaction Steps

A solution of ethyl 2-[3-(1-adamantyl)-4-benzyloxyphenyl]-5-(carbethoxymethylamino)pyrimidine (51 mg, 0.10 mmol), 1.0 M BBr3 (0.56 mmol) in CH2Cl2 (0.6 mL) and CH2Cl2 (1.4 mL) was stirred at −78° C. under argon for 2 h, quenched with H2O (10 mL) and extracted with EtOAc (100 mL). The extract was washed (water and brine) and dried. After solvent removal at reduced pressure, the residue was chromatographed (1:4 EtOAc/hexane) to give 41.6 mg (99%) of 2-[3-(1-adamantyl)-4-hydroxyphenyl]-5-(carbethoxymethylamino)pyrimidine as a pale-tan solid, mp 190° C. (dec). IR 3432, 2904, 1708, 1211 cm−1; 1H NMR (CDCl3) δ 1.32 (t, J=7.2 Hz, 3H, OCH2CH3), 1.79 (bs, 6H, AdCH2), 2.09 (bs, 3H, AdCH), 2.21 (m, 6H, AdCH2), 4.30 (q, J=7.2 Hz, 2H, OCH2CH3), 4.60 (m, 1H, NH), 4.72 (s, 2H, NHCH2CO), 5.85 (s, 1H, OH), 6.71 (d, J=8.4 Hz, 1H, 5′-ArH), 8.03 (dd, J=8.4 Hz, 2.1 Hz, 1H, 6′-ArH), 8.27 (d, J=2.1 Hz, 1H, 2′-ArH), 8.45 ppm (s, 2H, 4-ArH, 6-ArH). HRMS calcd C24H29N3O3 [M+H]+ 408.2287. found 408.2291.

Provenance & Evidence