Methyl iodide → Tert-butyl methyl(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)carbamate

HRID 881524Notes

Reaction equation

HRID 881524 reaction equation
[CH3:1][C:2]1([CH3:23])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][C:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[N:13][CH:14]=2)[O:3]1.CI.[C:26](=O)([O-])[O-].[Cs+].[Cs+]>>[CH3:26][N:15]([C:12]1[N:11]=[CH:10][C:9]([B:4]2[O:3][C:2]([CH3:23])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:14][N:13]=1)[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 177502232-(tert-Butoxycarbonylamino)pyrimidine-5-boronic acid, pinacol ester

Product 1

HCID 58234002Tert-butyl methyl(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)carbamate

Procedure

Tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-ylcarbamate (250 mg) was treated with 3 equivalents methyl iodide and cesium carbonate at room temperature for one hour. The crude reaction mixture was extracted with ethyl acetate and water. The initial organic layer is discarded. The aqueous layer was acidified to pH 5 and the product was extracted out of the aqueous with ethyl acetate. This organic layer was dried with magnesium sulfate, filtered and concentrated to give 150 mg crude tert-butyl methyl5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-ylcarbamate.

Workup

  1. customThe crude reaction mixture
  2. extractionwas extracted with ethyl acetate and water
  3. extractionthe product was extracted out of the aqueous with ethyl acetate
  4. dry with materialThis organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-46a071b5b1934185b2839ab153d1051f
Source dataset
uspto-grants-2015_03
Patent number
US08993563B2

Reaction notes

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