N-Iodosuccinimide → HCID 178478354, compound

Participants

Reaction Steps

To a solution of 2,4-dichloro pyrrolo[3,2-d]pyrimidine 19 (100 mg, 0.53 mmol) in anhydrous THF (5 mL), NIS (144 mg, 0.64 mmol) was added under N2 atmosphere and stirred for 2 h after which TLC indicated consumption of 19. The solvent was removed in vacuo and the residue dissolved in EtOAc. The organic phase was washed with aq. solution of Na2S2O3 followed by water, brine and then dried over MgSO4. The organic layer was concentrated in vacuo and loaded on silica. The product 20 was purified using column chromatography eluting with 9:1 hexanes/EtOAc to obtain product as off-white solid (90 mg, 54%). Rf 0.55 in 3:1 hexanes/EtOAc. Mp decomposed from 160-230° C. 1H NMR (400 MHz, DMSO-d6): δ 8.29 (s, 1H), 13.19 (s, 1H, NH). 13C NMR (400 MHz, DMSO-d6): δ 58.2, 124.4, 140.9, 143.5, 149.8, 153.5. ESI-MS m/z for calculated [M+H]+ 313.8743. found 313.8740.

Provenance & Evidence