5-Chlorouracil → 5-chloro-N-hexyl-2,4-dioxo-pyrimidine-1-carboxamide

HRID 1486526Notes

Reaction equation

[Cl:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[CH2:10]([N:16]=[C:17]=[O:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]>>[Cl:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[N:6]([C:17]([NH:16][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:18])[CH:7]=1

Participants

Reactant 2

HCID 157585-Chlorouracil

HCID 75659Hexyl isocyanate

Product 1

HCID 717182255-chloro-N-hexyl-2,4-dioxo-pyrimidine-1-carboxamideYield 31%

Procedure

The title compound was obtained according to the procedure described for the synthesis of Example 1, starting from 5-chlorouracil (0.10 g, 0.68 mmol); 1.2 equivalents of hexyl isocyanate were used herein. The crude was purified by column chromatography using a Teledyne ISCO apparatus (petroleum ether:EtOAc from 70:30 to 50:50) to afford the title compound (0.06 g, 31%) as white powder. 1H NMR (400 MHz, DMSO-d6): δ 0.86 (t, J=6.8 Hz, 3H), 1.21-1.35 (m, 6H), 1.46-1.54 (m, 2H), 3.24-3.29 (m, 2H), 8.41 (s, 1H), 9.07 (t, J=5.3 Hz, 1H), 12.24 (s, 1H). 13C NMR (101 MHz, DMSO-d6) δ 13.85, 21.97, 25.81, 28.57, 30.82, 40.55, 109.55, 135.56, 149.21, 150.61, 158.78. MS (ESI) m/z: 272 [M-H]−.

Workup

customdescribed for the synthesis of Example 1
customThe crude was purified by column chromatography

Sources & evidence

ORD record: ord-4934f0602f1c42c49807aae49c05c567
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428465B2

Reaction notes

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