8-Phenyloctan-1-ol → HCID 18470249, compound

HRID 2228922Notes

Reaction equation

HRID 2228922 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+](N[C:20]1[NH:25][C:24](=[O:26])[C:23]([CH2:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)=[CH:22][N:21]=1)([O-])=O>N1C=CC=CC=1>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:20]2[NH:25][C:24](=[O:26])[C:23]([CH2:27][C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)=[CH:22][N:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 5178508-Phenyloctan-1-olHCID 12788688N-{6-Oxo-5-[(pyridin-3-yl)methyl]-1,6-dihydropyrimidin-2-yl}nitramide

Product 1

HCID 18470249HCID 18470249, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 8-phenyl-1-octanol (1.5 g), 2-nitroamino-5-(pyrid-3-ylmethyl)pyrimidin-4-one (1.0 g) and pyridine (5 ml) was stirred at reflux for 24 hours, then the pyridine was removed by evaporation. Water was added, and the product extracted into dichloromethane, which was dried and evaporated. The residue was purified by chromatography (silica, 0-5% methanol in dichloromethane) and recrystallisation from ether to give 2-(8-phenyloct-1-yl)oxy-5-(pyrid-3-ylmethyl)pyrimidin-4-one as a pale buff solid (0.1 g). MPt 53-55° C.; 1H-NMR (CDCl3) δ 1.32 (8H, m), 1.60 (2H, m), 1.74 (2H, m), 2.58 (2H, t), 3.72 (2H, t), 4.31 (2H, t), 7.1-7.3 (6H, m), 7.54 (1H, m), 7.63 (1H, m), 8.45 (1H, m) and 8.55 (1H, d); MS (EI) Found M=391; C24H29N3O2 requires 391.

Workup

  1. temperatureat reflux for 24 hours
  2. customthe pyridine was removed by evaporation
  3. additionWater was added
  4. extractionthe product extracted into dichloromethane, which
  5. customwas dried
  6. customevaporated
  7. customThe residue was purified by chromatography (silica, 0-5% methanol in dichloromethane) and recrystallisation from ether

Sources & evidence

ORD record
ord-0f29d565bfb741238df314e2d4d5134b
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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