2-(Dimethylamino)ethanol → 4'-(2-(dimethylamino)ethoxy)-6',7'-dihydro-5'H-spiro[cyclopentane-1,8'-quinazolin]-2'-amine

Participants

Reaction Steps

A solution of 2-(dimethylamino)ethanol (63.9 μL, 0.631 mmol) in THF (5 mL) was treated with potassium tert-butoxide (78 mg, 0.694 mmol) at 0° C., and the reaction mixture was stirred for 30 minutes at ambient temperature. It was then treated with a solution of the product from Example 14A (30 mg, 0.126 mmol) in THF (2 mL) at ambient temperature, and the whole was stirred for 2 hours. The mixture was diluted with CH2Cl2 (20 mL) and H2O (10 mL), then the organic layer was separated, dried with MgSO4, and concentrated under reduced pressure. The resulting residue was chromatographed on silica gel, eluting with NH4OH/MeOH/CH2Cl2 (0.8/7.2/92), to afford the title product. 1H NMR (300 MHz, CDCl3) δ 4.56 (s, 2 H), 4.37 (t, 2 H), 2.68 (t, J=5.93 Hz, 2 H), 2.43 (t, J=6.10 Hz, 2 H), 2.32 (s, 6 H), 2.01-2.13 (m, 2 H), 1.79-1.90 (m, 2 H), 1.59-1.74 (m, 6 H), 1.47-1.57 (m, 2 H). MS (DCI+) m/z 291 (M+H).

Provenance & Evidence