Lithium Hexamethyldisilazide → 7-(1-Ethyl-propoxy)-1,5-dimethyl-3-(2,4,6-trimethyl-phenyl)-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

HRID 968020Notes

Reaction equation

[CH2:1]([CH:3]([O:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]2[N:14]([C:18]3[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=3[CH3:26])[C:15](=[O:17])[NH:16][C:8]=12)[CH2:4][CH3:5])[CH3:2].[CH3:27][Si]([N-][Si](C)(C)C)(C)C.[Li+]>>[CH2:1]([CH:3]([O:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]2[N:14]([C:18]3[C:19]([CH3:26])=[CH:20][C:21]([CH3:25])=[CH:22][C:23]=3[CH3:24])[C:15](=[O:17])[N:16]([CH3:27])[C:8]=12)[CH2:4][CH3:5])[CH3:2]

Participants

Reactant 2

HCID 2733832Lithium Hexamethyldisilazide

HCID 21912303HCID 21912303, compound

Product 1

HCID 219120937-(1-Ethyl-propoxy)-1,5-dimethyl-3-(2,4,6-trimethyl-phenyl)-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

Procedure

The title compound was prepared by reacting 7-(1-ethyl-propoxy)-5-methyl-3-(2,4,6-trimethyl-phenyl)-1,3-dihydro-imidazo[4,5-b]pyridin-2-one with lithium bis(trimethylsilyl)amide, followed by quenching with methyl iodide. Mp. 151-153° C. Anal. For C22H29N3O2. ¼H2O calc. C, 71.03; H, 7.99; N, 11.30; found: C, 71.29; H, 8.01; N, 11.02.

Workup

customby quenching with methyl iodide

Sources & evidence

ORD record: ord-0b506b33111a4934a4673e608bac6dc3
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06956047B1

Reaction notes

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