Isobutyl chloroformate → HCID 72548723, compound

HRID 1486545Notes

Reaction equation

HRID 1486545 reaction equation
[Br:1][C:2]1[C:3](=[O:18])[NH:4][C:5](=[O:17])[N:6]([C:8]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:9])[CH:7]=1.Cl[C:20]([O:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[O:21]>N1C=CC=CC=1>[Br:1][C:2]1[C:3](=[O:18])[N:4]([C:20]([O:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[O:21])[C:5](=[O:17])[N:6]([C:8](=[O:9])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:7]=1

Participants

4

Reactant 2

HCID 62365Isobutyl chloroformateHCID 71654962HCID 71654962, compound

Product 1

HCID 72548723HCID 72548723, compoundYield 132.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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]−.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-441a5ea1cd3449cbbb0f5fbe7083219f
Source dataset
uspto-grants-2016_08
Patent number
US09428465B2

Reaction notes

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