2,2'-Bipyridine → HCID 86696636, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of cyclopropylboronic acid (0.369 g, 44 mmol), 2-amino-6-chloro-9-(2-hydroxyethyl)-7H-purin-8-one (5 g, 22 mmol) and Na2CO3 (0.462 g, 44 mmol) were taken in dichloroethane (20 ml) and dimethylformamide (10 ml). A suspension of Cu(OAc)2 (0.399 g, 22 mmol) and bipyridine (0.343 g, 22 mmol) in hot dichloroethane (30 ml) was added to the above mixture. The mixture was stirred at 70° C. for 18 hours under air. The resulting mixture was cooled to room temperature, and a saturated aqueous NH4Cl solution was added, followed by water. The organic layer was separated and the aqueous layer was extracted three times with DCM. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to get crude 2-amino-6-chloro-7-cyclopropyl-9-(2-hydroxyethyl)purin-8-one (1.6 g, 27%) as an off white solid. 1HNMR (400 MHz, DMSO d6): δ 0.97-1.02 (m, 4H); 2.89-2.92 (m, 1H); 3.61-3.67 (m, 2H); 3.71-3.74 (m, 2H); 4.83 (t, J=12.8 Hz, 1H); 6.67 (bs, 2H)

Provenance & Evidence