Dichloromethane → (S)-4-(2-chloro-8-iodo-9-methyl-9H-purin-6-yl)-3-methylmorpholine

Participants

Reaction Conditions

Reaction Steps

To (S)-4-(2-chloro-9-methyl-9H-purin-6-yl)-3-methylmorpholine (750.0 mg, 2.80 mmol) in anhydrous THF (16 mL) at −78° C. under N2 was added freshly prepared lithium diisopropylamide in THF (2.0 eq). The resultant wine colored reaction was stirred at −78° C. After 1 h iodine monochloride in dichloromethane (4.2 mL, 4.2 mmol, 1.0 M, 1.5 eq.) was added and stirred at RT for 16 h. The reaction mixture was quenched with saturated aqueous sodium thiosulfate. Volatile solvent was then evaporated in vacuo, and the crude was diluted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water and brine, then dried (Na2SO4), filtered and evaporated in vacuo. The resultant residue was purified by column chromotagraphy (Si-PPC, gradient 0 to 100% ethyl acetate in hexane) to give the desired compound as a solid (446.4 mg, 40.5%). 1H NMR (CDCl3, 400 MHz) δ ppm 5.28 (broad s, 2H), 3.99 (m, 1H), 3.75 (m, 2H), 3.67 (s, 3H), 3.59 (m, 1H), 3.49 (broad s, 1H), 1.38 (d, 3H); LC-MS m/z (method A)=394/396 [M+H]+, RT=1.92 min.

Provenance & Evidence