Triethylamine → HCID 59152162, compound

HRID 605590Notes

Reaction equation

HRID 605590 reaction equation
[C:1]([N:5]1[C:9]([NH:10][C:11]2[CH:16]=[N:15][CH:14]=[C:13](Cl)[N:12]=2)=[CH:8][CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH:18]([B-](F)(F)F)=[CH2:19].[K+].C(N(CC)CC)C>C(O)CC>[C:1]([N:5]1[C:9]([NH:10][C:11]2[CH:16]=[N:15][CH:14]=[C:13]([CH:18]=[CH2:19])[N:12]=2)=[CH:8][CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 59152183N-(1-(tert-Butyl)-1H-pyrazol-5-yl)-6-chloropyrazin-2-amine

Product 1

HCID 59152162HCID 59152162, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 65.04 g of N-(1-tert-butyl-1H-pyrazol-5-yl)-6-chloropyrazin-2-amine, 41.6 g of potassium vinyltrifluoroborate, 4.22 g of (1,1′-bis (diphenylphosphino)ferrocene)dichloropalladium(II) dichloromethane complex, 72 ml of triethylamine and 685 ml of 1-propanol was stirred at 110° C. overnight, followed by cooling down to room temperature and concentrated in vacuo. The obtained residue was diluted with ethyl acetate, and an insoluble matter was filtered off using Celite. The resulting ethyl acetate solution was washed with water, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo. The obtained residue was suspended in 100 ml of ethyl acetate, and 400 ml of diisopropylether was added to the mixture. The obtained precipitate was collected to give the title compound as a pale brown solid.

Workup

  1. temperatureby cooling down to room temperature
  2. concentrationconcentrated in vacuo
  3. additionThe obtained residue was diluted with ethyl acetate
  4. filtrationan insoluble matter was filtered off
  5. washThe resulting ethyl acetate solution was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. addition400 ml of diisopropylether was added to the mixture
  10. customThe obtained precipitate was collected

Sources & evidence

ORD record
ord-796fb5c675cc485293f5af6b0cf0d8dd
Source dataset
uspto-grants-2011_03
Patent number
US07915263B2

Reaction notes

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