Potassium Phosphate, Tribasic → HCID 70654521, compound

HRID 1472502Notes

Reaction equation

HRID 1472502 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([NH2:9])=[N:6][C:7]=1Cl.[F:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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.O1CCOCC1>[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[N:3]=[CH:4][C:5]([NH2:9])=[N:6][C:7]=2[C:14]2[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2856454-Fluorophenylboronic acidHCID 181802075-Bromo-6-chloropyrazin-2-amine

Product 1

HCID 70654521HCID 70654521, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromo-6-chloropyrazin-2-amine (2 g, 9.66 mmol, 1.00 equiv), 4-fluorophenylboronic acid (3.38 g, 24.14 mmol, 2.50 equiv), Pd(PPh3)4 (1.11 g, 0.96 mmol, 0.10 equiv), K3PO4 (8.19 g, 38.66 mmol, 4.00 equiv), and 1,4-dioxane (10 mL) was stirred overnight at 100° C. in an oil bath. The resulting mixture was concentrated in vacuo, and the residue was purified via silica gel column chromatography (ethyl acetate: petroleum ether (1:20)), resulting in 1.7 g (62%) of 5,6-bis(4-fluorophenyl)pyrazin-2-amine as a brown solid.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. customthe residue was purified via silica gel column chromatography (ethyl acetate: petroleum ether (1:20))
  3. customresulting in 1.7 g (62%) of 5,6-bis(4-fluorophenyl)pyrazin-2-amine as a brown solid

Sources & evidence

ORD record
ord-eab1948422b34446bff1feaaebf9566b
Source dataset
uspto-grants-2015_04
Patent number
US09012637B2

Reaction notes

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