5-Bromouracil → HCID 71654962, compound

HRID 1486527Notes

Reaction equation

[O:1]=[C:2]1[NH:7][C:6](=[O:8])[CH:5]=[CH:4][N:3]1[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=CC=CC=1)=[O:10].[Br:22]C1C(=O)NC(=O)NC=1>>[Br:22][C:5]1[C:6](=[O:8])[NH:7][C:2](=[O:1])[N:3]([C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:21])=[O:10])[CH:4]=1

Participants

Reactant 2

HCID 58025-Bromouracil

HCID 72548263HCID 72548263, compound

Product 1

HCID 71654962HCID 71654962, compoundYield 62%

Procedure

The title compound was obtained according to the procedure described for the synthesis of compound of Example 1, starting from 5-bromouracil (0.03 g, 1.57 mmol). The crude was purified by column chromatography using a Teledyne ISCO apparatus (petroleum ether:EtOAc from 60:40 to 100% EtOAc) to afford the title compound (0.31 g, 62%) as white powder. 1H NMR (400 MHz, DMSO-d6): δ 0.87 (t, J=6.5 Hz, 3H), 1.24-1.32 (m, 6H), 1.40-1.61 (m, 2H), 3.26 (td, J=7.0, 5.7 Hz, 2H), 8.47 (s, 1H), 9.07 (t, J=5.7 Hz, 1H), 12.20 (s, 1H). 13C NMR (101 MHz, CDCl3): δ 14.12, 22.65, 26.61, 29.23, 31.49, 41.63, 100.15, 138.41, 148.91, 150.70, 158.08. MS (ESI) m/z: 317 [M-H]−.

Workup

customThe crude was purified by column chromatography

Sources & evidence

ORD record: ord-0a341c85dab240f69ecfdda2ac735ace
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428465B2

Reaction notes

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