Uracil → HCID 72548263, compound

HRID 1486524Notes

Reaction equation

HRID 1486524 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[C:9]1([CH2:15][CH2:16][CH2:17][CH2:18][N:19]=[C:20]=[O:21])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[O:3]=[C:2]1[NH:4][C:5](=[O:6])[CH:7]=[CH:8][N:1]1[C:20]([NH:19][CH2:18][CH2:17][CH2:16][CH2:15][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:21]

Participants

5

Reactant 2

HCID 1174UracilHCID 15932353(4-Isocyanatobutyl)benzene

Product 1

HCID 72548263HCID 72548263, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Uracil (0.10 g, 0.89 mmol) was dissolved in dry pyridine (4.4 mL). DMAP (0.12 g, 0.96 mmol) was added and the reaction mixture was stirred under nitrogen atmosphere at room temperature for 30 min. 4-Phenyl butyl isocyanate (0.27 mL, 1.60 mmol, 1.8 equiv) was then added and the resulting mixture was stirred for 12 hrs. The solvent was evaporated under reduced pressure and the crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc from 50:50 to 30:70) to afford the title compound (0.10 g, 59%) as white powder. 1H NMR (400 MHz, CDCl3): δ 1.59-1.82 (m, 4H), 2.66 (t, J=7.2 Hz, 2H), 3.29-3.60 (m, 2H), 5.89 (d, J=8.5 Hz, 1H), 7.11-7.22 (m, 3H), 723-734 (m, 2H), 8.41 (d, J=8, 5 Hz, 1H), 8.66 (s, 1H), 9.06 (t, J=5.7 Hz, 1H). 13C NMR (101 MHz, CDCl3): δ 28.69, 28.92, 35.56, 41.23, 77.16, 104.01, 126.06, 128.53, 139.08, 141.95, 149.84, 151.51, 162.30 MS (ESI) m/z: 310 [M-N]−.

Workup

  1. stirringthe resulting mixture was stirred for 12 hrs
  2. customThe solvent was evaporated under reduced pressure
  3. customthe crude was purified by column chromatography

Sources & evidence

ORD record
ord-8020b61dbffe4df99fbc3b1905f31faa
Source dataset
uspto-grants-2016_08
Patent number
US09428465B2

Reaction notes

Loading…