Dibutyltin oxide → HCID 178441717, compound

HRID 1182813Notes

Reaction equation

HRID 1182813 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([CH3:33])[N:8]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[C:9](=[O:26])[C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4].C[Si]([N:38]=[N+:39]=[N-:40])(C)C.C([Sn](=O)CCCC)CCC>>[NH:38]1[C:24]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[C:15]2[CH:14]=[CH:13][C:12]([CH2:11][C:10]3[C:9](=[O:26])[N:8]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=4)[C:7]([CH3:33])=[N:6][C:5]=3[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:17][CH:16]=2)=[N:25][N:40]=[N:39]1

Participants

4

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 66706063HCID 66706063, compound2×

Product 1

HCID 178441717HCID 178441717, compoundYield 61%

Conditions

Temperature
80 °C

Procedure

Process 3: To the toluene (3 mL) solution of 4′-{[4-butyl-2-methyl-6-oxo-1-(pyridin-2-yl)-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrile (335 mg, 0.77 mmol), trimethylsilylazide (2.64 g, 22.9 mmol) and dibutyltin oxide (96 mg, 0.386 mmol) were added, and stirred at 80° C. for 24 hrs under argon atmosphere. The reaction solvent was distilled off and the resulting residues were separated and purified by silica gel column chromatography (chloroform:methanol=100:1) to obtain the target compound (224 mg, 61%) as a pale yellow amorphous.

Workup

  1. distillationThe reaction solvent was distilled off
  2. customthe resulting residues were separated
  3. custompurified by silica gel column chromatography (chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-a8c66df13ba14ec8b0b57f761bd91471
Source dataset
uspto-grants-2014_03
Patent number
US08664226B2

Reaction notes

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