Cyanoacetamide → 4-(((Tert-butyldimethylsilyl)oxy)methyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 1530274Notes

Reaction equation

HRID 1530274 reaction equation
[Si:1]([O:8][CH2:9][C:10]#[C:11][C:12](=O)[CH3:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:15]([CH2:17][C:18]([NH2:20])=[O:19])#[N:16].N1(CC([O-])=O)CCCCC1>C(O)C.O>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH3:13])[NH:20][C:18](=[O:19])[C:17]=1[C:15]#[N:16])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 7898CyanoacetamideHCID 12764994HCID 12764994, compoundHCID 18315696HCID 18315696, compound

Product 1

HCID 682948094-(((Tert-butyldimethylsilyl)oxy)methyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrileYield 32.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of compound 5-((tert-butyldimethylsilyl)oxy)pent-3-yn-2-one (13.0 g, 61.0 mmol) and cyanoacetamide (6.2 g, 73.2 mmol) in a mixture of ethanol and water (9:1) (270 mL) at room temperature was added piperidineacetate (catalytic) and the reaction mixture was heated to reflux for 5 h. After removal of solvent water was added and the solid product was filtered. The solid product on washing with water followed by ether and hexane afforded the desired compound (5.5 g, 32%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 5 h
  3. customAfter removal of solvent water
  4. additionwas added
  5. filtrationthe solid product was filtered
  6. washThe solid product on washing with water

Sources & evidence

ORD record
ord-f321dcd9d4184c89a029070044fdc785
Source dataset
uspto-grants-2015_07
Patent number
US09090562B2

Reaction notes

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