1H-Pyrazole, 1-methyl- → HCID 89962884, compound

HRID 338000Notes

Reaction equation

HRID 338000 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[N:3]1.C([Li])CCC.[C:12]([Si:16]([CH3:26])([CH3:25])[O:17][C@@H:18]1[CH2:24][CH2:23][C@@H:22]2[C@@H:20]([O:21]2)[CH2:19]1)([CH3:15])([CH3:14])[CH3:13]>C1COCC1>[Si:16]([O:17][C@H:18]1[CH2:19][C@H:20]([OH:21])[C@@H:22]([C:6]2[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=2)[CH2:23][CH2:24]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 702551H-Pyrazole, 1-methyl-HCID 131732052HCID 131732052, compoundHCID 178418339Butyllithium

Product 1

HCID 89962884HCID 89962884, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 4a by using the 1-methylpyrazole (500 mg, 6.09 mmol), n-butyl lithium (2.69 M solution in hexane, 2.37 mL, 6.37 mmol), tert-butyl(dimethyl) [(1S*,3R*,6R*)-7-oxabicyclo[4.1.0]hept-3-yloxy]silane (J. Pharm. Pharmacol., 49, 835-842, 1997; 1.32 g, 5.78 mmol) and THF (30 mL), to yield the title compound (932 mg, 52%) as a colorless solid.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-ec99373a8018471e9750ebb64e3747d5
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

Loading…