Tetrahydro-4H-pyran-4-ol → 2-Chloro-5-iodo-4-((tetrahydro-2H-pyran-4-yl)oxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

2,4-Dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (1 equiv), tetrahydro-2H-pyran-4-ol (1.05 equiv), sodium tert-butoxide (1.05 equiv) and 1,4-dioxane (0.56 M) were combined and heated at 70° C. for 5 h. The reaction mixture was concentrated and extracted with ethyl acetate/H2O. The organic layers were combined, evaporated under reduced pressure and purified by silica-gel chromatography (0-50% hexane:ethyl acetate over 800 mL) followed by 5-15% (DCM:MeOH over 800 mL). Pure fractions were combined, evaporated under reduced pressure and dried under high vacuum to give the title compound (86% yield) as a yellow oil. 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.57 (s, 1H), 5.62-5.70 (m, 1H), 5.59 (s, 2H), 4.11-4.19 (m, 2H), 3.74-3.82 (m, 2H), 3.62 (d, J=8.20 Hz, 2H), 2.15-2.24 (m, 2H), 1.91-2.01 (m, 2H), 0.90-0.98 (m, 2H), 0.00 (s, 9H); MS (ESI) m/z 510.2 [M+1]+.

Provenance & Evidence