3-Pentanol → HCID 10269405, compound

HRID 2183538Notes

Reaction equation

HRID 2183538 reaction equation
[H-].[Na+].[CH3:3][CH2:4][CH:5]([OH:8])[CH2:6][CH3:7].Cl[C:10]1[N:15]2[N:16]=[C:17]([CH3:28])[C:18]([C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[CH3:27])=[C:14]2[N:13]=[C:12]([CH3:29])[CH:11]=1>CS(C)=O>[CH2:4]([CH:5]([O:8][C:10]1[N:15]2[N:16]=[C:17]([CH3:28])[C:18]([C:19]3[C:20]([CH3:27])=[CH:21][C:22]([CH3:26])=[CH:23][C:24]=3[CH3:25])=[C:14]2[N:13]=[C:12]([CH3:29])[CH:11]=1)[CH2:6][CH3:7])[CH3:3]

Participants

5

Reactant 3

HCID 114283-PentanolHCID 24758Sodium hydrideHCID 22474364HCID 22474364, compound

Product 1

HCID 10269405HCID 10269405, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
88 °C

Procedure

To a suspension of 60% Sodium hydride in oil (160 mg) in 4 ml of DMSO was added 3-pentanol (853 mg), and then 7-chloro-2,5-dimethyl-3-(2,4,6-trimethyl-phenyl)-pyrazolo[1,5-a]pyrimidine (580 mg) at room temperature. The mixture was heated at 88° C. overnight. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated and purified through silica gel column chromatography using 10% hexane in chloroform as eluent to give the title compound as an orange oil. 1H NMR (CDCl3) ä 6.96(s, 2H), 5.95(s, 1H), 4.52(m, 1H), 2.48(s, 3H), 2.33(s, 3H), 2.27(s, 3H), 2.03(s, 6H), 1.75-2.00(m, 4H), 1.08(t, 6H)ppm.

Workup

  1. customat room temperature
  2. customThe mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. custompurified through silica gel column chromatography

Sources & evidence

ORD record
ord-9b78abe95ed349f39b8dcf68ee088918
Source dataset
uspto-grants-2005_05
Patent number
US06900217B2

Reaction notes

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