Toluene → HCID 178438428, compound

HRID 520095Notes

Reaction equation

HRID 520095 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][N:5]2[C:10]([CH2:11][CH2:12][CH3:13])=[C:9]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[C:22]([C:27]#[N:28])=[CH:23][CH:24]=[CH:25][CH:26]=4)=[CH:17][CH:16]=3)[C:8](=[O:29])[N:7]([CH:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[C:6]=12.C([Sn](=O)CCCC)CCC.[N:46]([Si](C)(C)C)=[N+:47]=[N-:48].C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH3:1][C:2]1[CH:3]=[N:4][N:5]2[C:10]([CH2:11][CH2:12][CH3:13])=[C:9]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]4[NH:48][N:47]=[N:46][N:28]=4)=[CH:19][CH:20]=3)[C:8](=[O:29])[N:7]([CH:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[C:6]=12

Participants

6

Reactant 4

HCID 1140TolueneHCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 67008859HCID 67008859, compound

Product 1

HCID 178438428HCID 178438428, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4′-{[3-methyl-5-oxo-7-propyl-4-(tetrahydro-2H-pyran-4-yl)-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (0.33 g), dibutyltin oxide (0.088 g), azidotrimethylsilane (3.5 g) and toluene (30 mL) was stirred at 110° C. for 48 hr. The reaction mixture was diluted with ethyl acetate, washed with water and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as colorless crystals (0.15 g, 41%).

Workup

  1. washwashed with water
  2. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-85a6cf5bffbf46bc8fb38d9a249a8120
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Reaction notes

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