Potassium Carbonate → 5-(2-(3-((tert-butyldimethylsilyl)oxy)propyl)-2H-tetrazol-5-yl)-3-iodopyridin-2-amine

HRID 2199617Notes

Reaction equation

[I:1][C:2]1[C:3]([NH2:13])=[N:4][CH:5]=[C:6]([C:8]2[N:9]=[N:10][NH:11][N:12]=2)[CH:7]=1.Br[CH2:15][CH2:16][CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[Si:19]([O:18][CH2:17][CH2:16][CH2:15][N:10]1[N:11]=[N:12][C:8]([C:6]2[CH:7]=[C:2]([I:1])[C:3]([NH2:13])=[N:4][CH:5]=2)=[N:9]1)([C:22]([CH3:23])([CH3:24])[CH3:25])([CH3:21])[CH3:20]

Participants

Conditions

Temperature: 80 °C

Procedure

The reaction mixture of 3-iodo-5-(2H-tetrazol-5-yl)pyridin-2-amine (0.61 g, 2.12 mmol, 1 eq), (3-bromopropoxy)-tert-butyldimethylsilane (0.66 mL, 1.3 eq), and potassium carbonate (0.44 g, 1.5 eq) in anhydrous dimethylformamide (8 mL) was stirred and heated at 80° C. under nitrogen atmosphere for 2 hours. It was then diluted with ethyl acetate, washed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, and brine, and dried with anhydrous sodium sulfate. The upper clear solution was decanted and concentrated under reduced pressure with silica gel. A gradient column chromatography [Hexane to EtOAc-Hex (1:2)] rendered 5-(2-(3-((tert-butyldimethylsilyl)oxy)propyl)-2H-tetrazol-5-yl)-3-iodopyridin-2-amine as a white solid in the amount of 797 mg.

Workup

washwashed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, and brine
dry with materialdried with anhydrous sodium sulfate
customThe upper clear solution was decanted
concentrationconcentrated under reduced pressure with silica gel

Sources & evidence

ORD record: ord-061b2277407441fd9f8054bf99fbdb35
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359336B2

Reaction notes

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