Acetone → 7-[(3aS,4R,6R,6aR)-2,2-dimethyl-6-[(propan-2-ylamino)methyl]-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Participants

Reaction Steps

7-[(3aS,4R,6R,6aR)-6-(Aminomethyl)-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (1.024 g, 3.38 mmol) was dissolved in DCE (35 ml) and propan-2-one (0.50 ml, 6.75 mmol) was added and the reaction left for 15 mins. Sodium triacetoxyborohydride (1.002 g, 4.73 mmol) was added and the reaction left overnight. The reaction was quenched by the addition of sat. Na2CO3 solution (35 ml) and DCM (35 ml). The organic layer was separated and the aqueous layer was extracted with DCM (3×35 ml). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give the crude product. The product was purified by silica flash column chromatography using between 100% DCM and 15% 2M NH3 in MeOH:85% DCM as eluent to give the product as a white foamy solid (0.941 g, 81%): MS (ESI+) for C18H27N5O2 m/z 346.1 [M+H]+, 368.1 [m+Na]+; LCMS: Compound in solvent front; 1H NMR (500 MHz, CDCl3) δ 8.32 (s, 1H), 7.04 (d, J=3.63 Hz, 1H), 6.36 (d, J=3.47 Hz, 1H), 5.08 (br. s., 2H), 4.87-5.02 (m, 2H), 4.54 (t, J=6.38 Hz, 1H), 2.80-2.90 (m, 2H), 2.70-2.80 (m, 1H), 2.46 (dt, J=12.77, 6.54 Hz, 1H), 2.30-2.37 (m, 1H), 2.17 (q, J=11.98 Hz, 1H), 1.57 (s, 3H), 1.31 (s, 3H), 1.09 (t, J=5.44 Hz, 6H).

Provenance & Evidence