Sodium Carbonate → HCID 59351136, compound

HRID 555838Notes

Reaction equation

HRID 555838 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Cl[C:8]1[C:13]([Cl:14])=[N:12][CH:11]=[CH:10][N:9]=1.[O:15]1[CH2:20][CH2:19][CH:18]=[C:17](B2OC(C)(C)C(C)(C)O2)[CH2:16]1>O1CCOCC1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:14][C:13]1[C:8]([C:17]2[CH2:16][O:15][CH2:20][CH2:19][CH:18]=2)=[N:9][CH:10]=[CH:11][N:12]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 785752,3-DichloropyrazineHCID 158366332-(5,6-dihydro-2H-pyran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 59351136HCID 59351136, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Sodium carbonate (6.48 mL, 12.95 mmol, 2.0 M in water) was added to a stirred mixture of 2,3-dichloropyrazine (1.28 mL, 8.63 mmol), 2-(5,6-dihydro-2H-pyran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.91 g, 4.32 mmol), and tetrakis(triphenylphosphine)palladium (0.50 g, 0.43 mmol) in dioxane (16 mL) under an argon atmosphere. The reaction mixture was stirred at 80° C. for 16 h before being cooled to room temperature and diluted with EtOAc. The mixture was washed with water, washed with sat. sodium chloride, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by silica gel chromatography to give 2-chloro-3-(5,6-dihydro-2H-pyran-3-yl)pyrazine. [M+1]=197.0.

Workup

  1. temperaturebefore being cooled to room temperature
  2. washThe mixture was washed with water
  3. washwashed with sat. sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-373d10e22956498daacb2d4d0dff7f24
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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