Dibutyltin oxide → tert-butyl (3S*,5R*)-3-[({2-tert-butyl-4-[(furan-2-ylmethyl)amino]pyrimidin-5-yl}carbonyl)(2-methylpropyl)amino]-5-(2H-tetrazol-5-yl)piperidine-1-carboxylate

HRID 2192816Notes

Reaction equation

HRID 2192816 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)[C:8]([C:18]([N:20]([CH2:36][CH:37]([CH3:39])[CH3:38])[C@H:21]2[CH2:26][C@@H:25]([C:27]#[N:28])[CH2:24][N:23]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:22]2)=[O:19])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[N:40]([Si](C)(C)C)=[N+:41]=[N-:42].C([Sn](CCCC)=O)CCC>>[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)[C:8]([C:18]([N:20]([CH2:36][CH:37]([CH3:39])[CH3:38])[C@H:21]2[CH2:26][C@@H:25]([C:27]3[N:40]=[N:41][NH:42][N:28]=3)[CH2:24][N:23]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:22]2)=[O:19])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 86649290HCID 86649290, compound

Product 1

HCID 86649291tert-butyl (3S*,5R*)-3-[({2-tert-butyl-4-[(furan-2-ylmethyl)amino]pyrimidin-5-yl}carbonyl)(2-methylpropyl)amino]-5-(2H-tetrazol-5-yl)piperidine-1-carboxylateYield 58.3%

Procedure

To tert-butyl (3S*,5R*)-3-[({2-tert-butyl-4-[(furan-2-ylmethyl)amino]pyrimidin-5-yl}carbonyl)(2-methylpropyl)amino]-5-cyanopiperidine-1-carboxylate (120 mg) were added azido(trimethyl)silane (55 mg) and dibutyl(oxo)stannane (5 mg), and the mixture was stirred with heating to reflux for 1 day. The reaction mixture was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (10:90-100:0) was concentrated under reduced pressure to give the object compound (75.5 mg).

Workup

  1. temperaturewith heating
  2. temperatureto reflux for 1 day
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. washthe fraction eluted with ethyl acetate-hexane (10:90-100:0)
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-fa99dfcc89314054b3899399a5b991b4
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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