Dibutyltin oxide → HCID 178441723, compound

HRID 629041Notes

Reaction equation

C[Si]([N:5]=[N+:6]=[N-:7])(C)C.C([Sn](=O)CCCC)CCC.[CH2:18]([C:22]1[N:23]=[C:24]([CH3:52])[N:25]([C:44]2[N:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][N:45]=2)[C:26](=[O:43])[C:27]=1[CH2:28][C:29]1[CH:30]=[CH:31][C:32]([C:35]2[CH:42]=[CH:41][CH:40]=[CH:39][C:36]=2[C:37]#[N:38])=[N:33][CH:34]=1)[CH2:19][CH2:20][CH3:21]>C1(C)C=CC=CC=1>[NH:5]1[C:37]([C:36]2[CH:39]=[CH:40][CH:41]=[CH:42][C:35]=2[C:32]2[N:33]=[CH:34][C:29]([CH2:28][C:27]3[C:26](=[O:43])[N:25]([C:44]4[N:45]=[CH:46][C:47]([O:50][CH3:51])=[CH:48][N:49]=4)[C:24]([CH3:52])=[N:23][C:22]=3[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:30][CH:31]=2)=[N:38][N:7]=[N:6]1

Participants

Conditions

Temperature: 95 °C

Procedure

Process 4: Trimethylsilyl azide (8.68 g, 75.3 mmol) and dibutyltin oxide (55 mg, 0.221 mmol) were added to toluene (20 mL) solution of 2-{5-{[4-butyl-1-(5-methoxypyrimidin-2-yl)-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl]methyl}pyridin-2-yl}benzonitrile (200 mg, 0.43 mmol) and stirred for 24 hours at 95° C. under argon atmosphere. The residues obtained by removing the reaction solvent by distillation was separated and purified by silica gel column chromatography (chloroform:methanol=100:1) to give 5-{{6-[2-(1H-tetrazol-5-yl)phenyl]pyridin-3-yl}methyl}-6-butyl-3-(5-methoxypyrimidin-2-yl)-2-methylpyrimidin-4(3H)-one (174 mg, 80%) as yellow oil.

Workup

customThe residues obtained
customby removing the reaction solvent
distillationby distillation
customwas separated
custompurified by silica gel column chromatography (chloroform:methanol=100:1)

Sources & evidence

ORD record: ord-210b8806db884bc686ffcc092d0db2fc
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315493B2

Reaction notes

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