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

HRID 577442Notes

Reaction equation

[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].C(O[K])(C)(C)C.[Si:13]([O:20][CH2:21][C:22]#[C:23][C:24](=O)[CH3:25])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>CS(C)=O>[Si:13]([O:20][CH2:21][C:22]1[CH:23]=[C:24]([CH3:25])[NH:6][C:4](=[O:5])[C:3]=1[C:1]#[N:2])([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of 2-cyanoacetamide (1.74 g, 20.7 mmol) and tBuOK (2.32 g, 20.7 mmol) in DMSO (48 mL) was added 5-{[tert-butyl(dimethyl)silyl]oxy}pent-3-yn-2-one (Cpd G, 4.4 g, 21.0 mmol) dropwise. The reaction mixture turned bright orange. The reaction mixture was stirred for 2 hours at 0° C., then quenched with NH4Cl (sat., aq.) and diluted with water causing solids to precipitate out. The solids were collected via filtration and dried under vacuum to give 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (Cpd H, 5.0 g, 86%) as a tan solid.

Workup

customquenched with NH4Cl (sat., aq.)
additiondiluted with water causing solids
customto precipitate out
filtrationThe solids were collected via filtration
customdried under vacuum

Sources & evidence

ORD record: ord-8edd1469bcfb4be1b0f7980c8d1e45c2
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040515B2

Reaction notes

Loading…