Uracil → HCID 72548490, compound

HRID 1486525Notes

Reaction equation

HRID 1486525 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[C:9]1([CH:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][N:17]=[C:18]=[O:19])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>ClCCl>[C:9]1([CH:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][NH:17][C:18]([N:1]2[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]2=[O:3])=[O:19])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 1174UracilHCID 122583912,2-Diphenylethyl isocyanate

Product 1

HCID 72548490HCID 72548490, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was obtained according to the procedure described for the synthesis of Example 1, starting from uracil (0.37 g, 3.34 mmol); 1.3 equivalents of 2,2-diphenylethyl isocyanate were used herein. The crude was taken up in dichloromethane; the title compound precipitated and was filtered off. The title compound (0.85 g, 76%) was isolated as white powder. 1H NMR (400 MHz, DMSO-d6): δ 3.97 (dd, J=8, 0, 5.5 Hz, 2H), 4.32 (t, J=7.9 Hz, 1H), 5.78 (d, J=8.4 Hz, 1H), 7.17-7.25 (m, 2H), 7.27-7.39 (m, 8H), 8.19 (d, J=8.4 Hz, 1H), 9.20 (t, J=5.5 Hz, 1H), 11.66 (s, 1H). 13C NMR (101 MHz, DMSO-d6): δ 44.93, 50.61, 103.98, 127.09, 127.18, 128.60, 138.79, 142.58, 142.91 150.27, 151.93, 161.03. MS (ESI) m/z: 334 [M-H]−.

Workup

  1. customdescribed for the synthesis of Example 1
  2. customthe title compound precipitated
  3. filtrationwas filtered off

Sources & evidence

ORD record
ord-1dcf824f5c334bb780815c0b468f7388
Source dataset
uspto-grants-2016_08
Patent number
US09428465B2

Reaction notes

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