Hydrochloric Acid → HCID 16019476, compound

Participants

Reaction Conditions

Reaction Steps

Pyrimidin-5-one 15m (560 mg, 1.55 mmol) was treated with 2-thiophenemethylamine (0.48 mL, 4.66 mmol, 3 equivalent), DBU (0.70 mL, 4.66 mmol, 3 equivalent) and PyBOP (2.43 g, 4.66 mmol, 3 equivalent) in anhydrous acetonitrile (5.1 mL), and placed in a microwave vessel. The mixture was heated in a microwave synthesizer at 100° C. for 30 min. The reaction mixture was treated with aqueous HCl (1 M, 20 mL) and stirred for 30 min before Na2CO3 was added to adjust pH to approximately 9. The reaction mixture was dissolved in CHCl3 (75 mL), washed with aqueous HCl (1 M, 3×75 mL). The organic product layer was concentrated in vacuo and UTBinh-14 was purified by flash column chromatography: dichloromethane+1% acetic acid→dichloromethane:methanol (100:1+1% acetic acid). The residue was re-crystallized from ethanol to yield UTBinh-14 (392 mg, 55% yield) as a white solid. 1H NMR (CDCl3, 500 MHz): δ 1.21 (t, 3H, J=10 Hz), 2.67 (q, 2H, J=10 Hz), 5.15 (d, 2H, J=5 Hz), 5.86 (t, 1H, J=5 Hz), 7.01 (dd, 1H, J=5 Hz), 7.23 (d, 1H, J=5 Hz), 7.26 (d, 1H, J=5 Hz), 7.28 (d, 2H, J=5 Hz), 7.88 (d, 1H, J=5 Hz), 7.95 (d, 1H, J=5 Hz), 8.12 (d, 2H, J=10 Hz). 13C NMR (CDCl3, 125 Hz): δ 15.73, 29.55, 41.04, 118.13, 126.42, 127.89, 128.07, 128.64, 129.08, 133.84, 153.22. HR-ESI-MS (M+H)+ calc 456.0622. found 456.0583 for C20H17N5O2S3.

Provenance & Evidence