Tert-butyl acetoacetate → N-(6-(tert-butyldimethylsilyloxymethyl)pyridin-2-yl)-3-oxobutanamide

HRID 1172408Notes

Reaction equation

[C:1]([O:7]C(C)(C)C)(=O)[CH2:2][C:3]([CH3:5])=[O:4].[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[N:14]=1>C1(C)C=CC=CC=1>[Si:21]([O:20][CH2:19][C:15]1[N:14]=[C:13]([NH:12][C:1](=[O:7])[CH2:2][C:3](=[O:4])[CH3:5])[CH:18]=[CH:17][CH:16]=1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 100 °C

Procedure

6.6 mL of tert-butyl acetoacetate was dissolved in 10 mL of toluene and the mixture was stirred at 100° C. for 1 hour. To the reaction solution was added a solution of 1.9 g (8.1 mmol) of 2-amino-6-(tert-butyldimethylsilyloxymethyl)pyridine in 5 mL of toluene and the mixture was stirred at the same temperature for 15 hours. The reaction solution was concentrated and the resulting residue was purified by a silica gel column chromatography to give 2.2 g of the title compound as a yellow oil.

Workup

stirringthe mixture was stirred at the same temperature for 15 hours
concentrationThe reaction solution was concentrated
customthe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record: ord-ecc318fbca184f06bc0289e0ea1934fa
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834018B2

Reaction notes

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