Pyridine → 3-Cyclopentyl-5-methyl-8-phenylimidazo[1,2-d][1,2,4]triazin-2-ol

HRID 396156Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[C:4]([CH3:14])[N:5]=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.N1C=CC=CC=1.Br[CH:22]([CH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)[C:23](Cl)=[O:24].C1(CC(Cl)=O)CCCC1>ClCCl>[CH:26]1([C:22]2[N:3]3[C:4]([CH3:14])=[N:5][N:6]=[C:7]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:2]3=[N:1][C:23]=2[OH:24])[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 5-amino-3-methyl-6-phenyl-[1,2,4]triazine (0.2 g, 1.07 mmol) in dichloromethane (20 ml) was added pyridine (0.104 ml, 1.28 mmol) followed by dropwise addition of 2-bromo-2-cyclopentylacetyl chloride (0.266 ml, 1.18 mmol; prepared from cyclopentylacetyl chloride by the method of Gleason, Tetrahedron Lett., 1970, 39, 3431). The reaction mixture was stirred for 18 h after which time the dichloromethane was evaporated in vacuo. The residue was dissolved in t-butanol (20 ml) to which was added triethylamine (1 ml) and sodium iodide (0.010 g) and the resultant mixture was heated at 120° C. for 18 h. The n-butanol was evaporated in vacuo and the residue was purified by flash chromatography (SiO2; 60% EtOAc in hexanes) to afford the title compound (0.178 g). δH (400 MHz; d6-DMSO) 1.40-2.20 (8H, m), 2.71 (3H, s), 3.65 (1H, m), 7.49 (3H, m), 8.05 (2H, m). m/z (ES+) 295 (M+1).

Workup

customwas evaporated in vacuo
dissolutionThe residue was dissolved in t-butanol (20 ml) to which
additionwas added triethylamine (1 ml) and sodium iodide (0.010 g)
customThe n-butanol was evaporated in vacuo
customthe residue was purified by flash chromatography (SiO2; 60% EtOAc in hexanes)

Sources & evidence

ORD record: ord-57a54e26bfbe4d898fe3452337f1aaac
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06608062B1

Reaction notes

Loading…