Water → HCID 54342136, compound

HRID 1789815Notes

Reaction equation

HRID 1789815 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14]Br)=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:17][C:18]1([CH3:28])[O:23][C:22](=[O:24])[CH:21]([CH2:25][CH3:26])[C:20](=[O:27])[O:19]1.C(N(CC)CC)C.O>CS(C)=O>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:21]2([CH2:25][CH3:26])[C:20](=[O:27])[O:19][C:18]([CH3:17])([CH3:28])[O:23][C:22]2=[O:24])=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 37577125-ethyl-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 23030321tert-Butyl (5-(bromomethyl)pyridin-2-yl)carbamate

Product 1

HCID 54342136HCID 54342136, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(5-Bromomethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (1.0 g, 3.48 mmol) was added to a solution of 2,2-dimethyl-5-ethyl-1,3-dioxane4,6-dione (600 mg, 3.48 mmol) and triethylamine (0.51 mL, 3.66 mmol) in dimethyl sulfoxide (40 mL) under nitrogen. The reaction mixture was stirred over night and water (100 mL) was added. Filtration of the precipitate gave [5-(5-ethyl-2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylmethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester (1.15 g, 87%).

Workup

  1. filtrationFiltration of the precipitate

Sources & evidence

ORD record
ord-436afded2b2d4ff79d62622977886f08
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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