1,4-Dioxane → 2-(4-[1,2,3]Triazol-1-yl-butyl)-pyrimidine-5-boronic acid

HRID 349228Notes

Reaction equation

O1CCOCC1.Br[C:8]1[CH:9]=[N:10][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]2[CH:22]=[CH:21][N:20]=[N:19]2)=[N:12][CH:13]=1.[B:23]1(B2OC(C)(C)C(C)(C)O2)[O:27]C(C)(C)C(C)(C)[O:24]1.C([O-])(=O)C.[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:18]1([CH2:17][CH2:16][CH2:15][CH2:14][C:11]2[N:10]=[CH:9][C:8]([B:23]([OH:27])[OH:24])=[CH:13][N:12]=2)[CH:22]=[CH:21][N:20]=[N:19]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of tris(dibenzylideneacetone)dipalladium(0) (0.027 g, 0.03 mmol in dioxane (6 ml) tricyclohexylphosphine (0.084 g, 0.30 mmol) is added and the mixture stirred under argon for 30 min. A solution of 5-bromo-2-(4-[1,2,3]triazol-1-yl-butyl)-pyrimidine (0.282 g, 1.0 mmol), bis(pinacolato)diboron (0.279 g, 1.1 mmol) and potassium acetate (0.147 g, 1.5 mmol) is added and the mixture is heated at 80° C. for 5 h. After cooling the mixture is concentrated in vacuo and the crude product is purified by flash column chromatography (ethyl acetate (100%)->ethyl acetate/tetrahydrofuran 1:1) yielding 2-(4-[1,2,3]triazol-1-yl-butyl)-pyrimidine-5-boronic acid as a beige solid. Yield 140 mg (57%).

Workup

temperatureAfter cooling the mixture
concentrationis concentrated in vacuo
customthe crude product is purified by flash column chromatography (ethyl acetate (100%)->ethyl acetate/tetrahydrofuran 1:1)

Sources & evidence

ORD record: ord-e177312e9c4c41f7be95aef4674fbc73
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179812B2

Reaction notes

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