1,2-Dichloroethane → Hydrochloric Acid

Participants

Reaction Steps

A solution of 1-{(R)-1-[9-((1R,2S,3R,4S)-4-amino-2,3-dihydroxy-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-3-pyridin-3-yl-urea (Example 26 step 2) (17 mg, 26 mmol) in DCE (1 ml) is treated with propanaldehyde (1.5 mg, 26 mmol) and placed under an atmosphere of argon. Sodium triacetoxyborohydride (10 mg, 51 μmol) is added and the reaction mixture is stirred at room temperature overnight. The mixture is quenched with 2M NaOH (5 drops) and the solvent is removed in vacuo. The residue is purified by C-18 reverse phase column chromatography eluting with acetonitrile:water:HCl (0.1%) (gradient of 20 to 100% acetonitrile) to yield the title compound. (MH+ 677.14)

Provenance & Evidence