Isobutyl chloroformate → Isobutyl 3-(hexylcarbamoyl)-2,6-dioxo-5-phenyl-pyrimidine-1-carboxylate
Reaction equation
[CH2:1]([NH:7][C:8]([N:10]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13](=[O:22])[NH:12][C:11]1=[O:23])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].Cl[C:25]([O:27][CH2:28][CH:29]([CH3:31])[CH3:30])=[O:26]>>[CH2:1]([NH:7][C:8]([N:10]1[CH:15]=[C:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:13](=[O:22])[N:12]([C:25]([O:27][CH2:28][CH:29]([CH3:31])[CH3:30])=[O:26])[C:11]1=[O:23])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]Participants
Procedure
The title compound was obtained according to the procedure described for the synthesis of Example 24, starting from N-hexyl-2,4-dioxo-5-phenyl-pyrimidine-1-carboxamide (Example 14) (0.05 g, 0.17 mmol); 9.0 equivalents of isobutyl chloroformate were used herein. Another portion of isobutyl chloroformate (9.0 equivalents) was added after 5 hrs and the reaction stirred at room temperature for 15 hrs. The crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc 90:10) to afford the title compound (0.043 g, 39%) as a clear, colorless oil. 1H NMR (400 MHz, CDCl3): δ 0.90 (t, J=6.8 Hz, 3H), 1.02 (d, J=6.8 Hz, 6H), 1.29-1.41 (m, 6H), 1.57-1.65 (m, 2H), 2.12 (h, J=6.7 Hz, 1H), 3.41 (td, J=7.1, 5.7 Hz, 2H), 4.27 (d, J=6.7 Hz, 2H), 7.36-7.45 (m, 3H), 7.53-7.57 (m, 3H), 8.57 (s, 1H), 8.96 (t, J=5.0 Hz, 1H). 13C NMR (101 MHz, CDCl3): δ 14.14, 18.96, 22.65, 26.63, 27.84, 29.26, 31.52, 41.65, 76.42, 116.58, 128.58, 128.78, 128.92, 131.19, 135.34, 149.45, 149.54, 149.78, 159.35. MS (ESI) m/z: 416 [M-H]+.
Workup
- customdescribed for the synthesis of Example 24
- customThe crude was purified by column chromatography
Sources & evidence
- ORD record
- ord-c4bb5b0545cf40e1a63d65b291a58b0a
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428465B2
Reaction notes
Loading…