Hydrogen Peroxide → HCID 89655801, compound

HRID 626148Notes

Reaction equation

HRID 626148 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:16]2[N:21]=[CH:20][C:19](B3OC(C)(C)C(C)(C)O3)=[CH:18][N:17]=2)=[O:15])=[CH:10][CH:9]=1.[OH:31]O>C1COCC1>[OH:31][C:19]1[CH:18]=[N:17][C:16]([C:14]([C:11]2[CH:12]=[CH:13][C:8]([O:7][CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)=[CH:9][CH:10]=2)=[O:15])=[N:21][CH:20]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 89672890HCID 89672890, compound

Product 1

HCID 89655801HCID 89655801, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-(tetrahydro-2H-pyran-2-yloxy)phenyl)(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)methanone (410 mg, 1 mmol) in 20 mL of THF was added 0.5 mL 33% H2O2 and the reaction was stirred for 1 h at rt. The reaction was then quenched with aq. Na2SO3, extracted with EtOAc, washed with water and brine, dried, filtered, concentrated, and purified by column chromatography to give the desired product (240 mg, 80% yield).

Workup

  1. customThe reaction was then quenched with aq. Na2SO3
  2. extractionextracted with EtOAc
  3. washwashed with water and brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-1020acfe7dd4450dbf9cde32a59e59e5
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

Loading…