Isobutyl chloroformate → HCID 72548723, compound

Participants

Reaction Steps

5-Bromo-N-hexyl-2,4-dioxo-pyrimidine-1-carboxamide (Example 5) (0.06 g, 0.18 mmol) was dissolved in dry pyridine (1.5 mL), and isobutyl chloroformate (0.03 mL, 0.21 mmol) was added at 0° C. The reaction was stirred at room temperature for 15 hrs, and the solvent was removed under reduced pressure. The crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc 85:15) to afford the title compound (0.10 g, 48%) as a clear, colorless oil. 1H, NMR (400 MHz, CDCl3): δ 0.89 (t, J=6.8 Hz, 3H), 1.01 (d, J=6.7 Hz, 6H), 1.28-1.38 (m, 6H), 1.57-1.64 (m, 2H), 2.11 (h, J=6.7 Hz, 1H), 3.39 (td, J=7.1, 5.7, 2H), 4.25 (d, J=6.6, 2H), 8.74 (s, 1H), 8.80 (t, J=4.6 Hz, 1H). 13C NMR (101 MHz, CDCl3): δ 14.12, 18.90, 22.63, 26.58, 27.81, 29.18, 31.47, 41.76, 76.84, 98.78, 137.72, 148.46, 148.55, 149.44, 156.04. MS (ESI) m/z: 289 [M-CONH(CH2)5CH3]−.

Provenance & Evidence