Diisopropylethylamine → HCID 178456316, compound

Participants

Reaction Conditions

Reaction Steps

(S)-1-(6-Fluoro-1-isopropyl-7-pyridin-2-yl-1H-benzoimidazol-2-yl)ethylamine (0.18 g, 0.6 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (145 mg, 0.60 mmol) and DIPEA (543 μL, 3.0 mmol) were added and the reaction mixture heated at 90° C. for 16 hours. The reaction mixture was loaded onto an SCX column to remove the THP group. The column was washed with MeOH and the product was eluted with 2M NH3 in MeOH. The product fractions were collected, concentrated in vacuo and the resultant residue was subjected to flash chromatography (SiO2, eluting with 0-10% methanol in DCM) to give 409 as a white solid (23 mg, 10%). LCMS (Method K): RT 2.94 min [M+H]+ 417. 1H NMR (DMSO-d6, 400 MHz): δ 12.69 (1H, br s), 8.69 (1H, d, J=4.4 Hz), 8.17 (1H, br s), 8.13 (1H, s), 7.93 (1H, td, J=7.8, 1.8 Hz), 7.66 (1H, dd, J=8.8, 5.0 Hz), 7.64 (1H, br s), 7.62 (1H, d, J=7.8 Hz), 7.47 (1H, ddd, J=7.7, 4.9, 1.1 Hz), 7.11 (1H, dd, J=10.2, 8.9 Hz), 5.90-5.78 (1H, m), 4.11-3.87 (1H, m), 1.62 (3H, d, J=6.6 Hz), 1.35-1.15 (6H, m)

Provenance & Evidence