Tetrabutylammonium Fluoride → HCID 67984007, compound

Participants

Reaction Steps

This compound was synthesized in an analogous manner to 21 utilizing benzyl 2-(tert-butyldiphenylsilyloxy)acetate in step one, and further TBDPS deprotection as the last step. To 4′-(tert-Butyl-diphenyl-silanyloxymethyl)-N2-pyridin-4-yl-[4,5]bipyrimidinyl-2,2′-diamine (150 mg, 0.281 mmol), TBAF (1N in THF) (562 μl, 0.562 mmol) was added. The reaction was stirred rt for 1 hour. Additional TBAF (1N in THF) (281 μl, 0.281 mmol) was added, and the reaction mixture was stirred for an additional 2 hours. The reaction was quenched by slow addition of saturated ammonium chloride and the volatiles were evaporated. The residue was then partitioned between water and EtOAc. The organic layer was washed with brine, dried with sodium sulfate, and concentrated. The crude product was purified by reverse-phase HPLC [100% aqueous phase to 60% organic phase over 15 minutes] to obtain the desired product as a slightly pale yellow solid (50 mg, 60% yield). 1H NMR (400 MHz, DMSO-d6) ppm 4.66 (d, J=2.53 Hz, 2 H) 5.04 (br. s., 1 H) 7.18 (s, 2 H) 7.30 (d, J=5.05 Hz, 1 H) 7.77 (d, J=6.06 Hz, 2 H) 8.36 (d, J=6.06 Hz, 2 H) 8.57 (d, J=5.56 Hz, 1 H) 8.63 (s, 1 H) 10.03 (s, 1 H). HRMS (ES+) for C14H13N7O.H+ [MH+]: calcd. 296.1260. found 296.1263. UV-LC: 100/100% UV purity at 214/254 nm; tR=2.87 minutes over 7.75 minutes

Provenance & Evidence