Trifluoromethyluracil → HCID 71655118, compound

HRID 1486556Notes

Reaction equation

HRID 1486556 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[C:4](=[O:10])[NH:5][C:6](=[O:9])[NH:7][CH:8]=1.[CH2:13]([N:21]=[C:22]=[O:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>>[CH2:13]([NH:21][C:22]([N:7]1[CH:8]=[C:3]([C:2]([F:11])([F:1])[F:12])[C:4](=[O:10])[NH:5][C:6]1=[O:9])=[O:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

3

Reactant 2

HCID 5899TrifluoromethyluracilHCID 76616Octyl isocyanate

Product 1

HCID 71655118HCID 71655118, compoundYield 22%

Procedure

The title compound was obtained according to the procedure described for the synthesis of Example 1, starting from 5-(trifluoromethyl) uracil (0.10 g, 0.55 mmol); 3.0 equivalents of octyl isocyanate were used herein. The crude was purified by column chromatography using a Teledyne ISCO apparatus (gradient from cyclohexane:EtOAc 70:30 to cyclohexane:EtOAc 60:40) and then washed with n-heptane to afford the title compound (0.04 g, 22%) as a white powder. 1H NMR (400 MHz, CDCl3) δ 0.88 (d, J=6.8 Hz, 3H), 1.18-1.44 (m, 10H), 1.53-1.70 (m, 2H), 3.41 (td, J=7.1, 5.5 Hz, 2H), 8.90-8.97 (m, 3H). 13C NMR (101 MHz, CDCl3) δ 14.20, 22.75, 26.92, 29.20, 29.26, 31.89, 41.80, 121.16 (q, J=268.7 Hz), 139.73, 148.25, 150.83, 156.86, MS (ESI) m/z 334 [M-H]+.

Workup

  1. customdescribed for the synthesis of Example 1
  2. customThe crude was purified by column chromatography
  3. washwashed with n-heptane

Sources & evidence

ORD record
ord-c0ff945182b746e6bcb8ff77320533c8
Source dataset
uspto-grants-2016_08
Patent number
US09428465B2

Reaction notes

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