Water → HCID 136247227, compound

Participants

Reaction Steps

A solution of 2-chloro-7-(2-hydroxyethyl)-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one (150 mg, 0.70 mmol, 1.00 equiv), 1-[2,6-difluoro-4-(2-methoxyethoxy)phenyl]piperazine (192 mg, 0.71 mmol, 1.00 equiv) and DIEA (182 mg, 1.41 mmol, 2.00 equiv) in ethanol (2 mL) was placed in an 8-mL sealed tube. The reaction mixture was irradiated with microwave radiation for 30 min at 140° C. and then cooled back to room temperature. The crude product was collected by filtration then purified by Prep-HPLC with the following conditions (Prep-HPLC-005): Column: XBridge Prep C18 OBD Column, 5 um, 19*150 mm; mobile phase: water with 10 mmol NH4HCO3 and MeCN (MeCN 35.0%, MeCN up to 50.0% in 10 min, up to 95.0% in 1 min, hold 95.0% in 1 min, down to 35.0% in 2 min); Detector, UV 254/220 nm to yield 98.3 mg (31%) of 2-[4-[2,6-difluoro-4-(2-methoxyethoxy)phenyl]piperazin-1-yl]-7-(2-hydroxyethyl)-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one as a white solid. 1HNMR (400 MHz, DMSO-d6) δ□ ppm 3.09-3.06 (m, 4H), 3.28 (s, 3H), 3.69-3.61 (m, 8H), 4.02-3.99 (m, 2H), 4.08-4.06 (m, 2H), 4.85 (t, J=5.6 Hz, 1H), 6.23 (d, J=3.2 Hz, 1H), 6.72 (d, J=11.2 Hz, 2H), 6.81 (d, J=3.2 Hz, 1H), 10.81 (s, 1H). LC-MS calcd. for C21H26F2N5O4 [(M+H)+] 450, obsd. 450.3.

Provenance & Evidence