Sodium Carbonate → 3-[4-(Cyclohexyloxy)phenyl]pyrazin-2-amine

HRID 1405712Notes

Reaction equation

HRID 1405712 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH:7]1([O:13][C:14]2[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Cl[C:24]1[C:25]([NH2:30])=[N:26][CH:27]=[CH:28][N:29]=1>O.COCCOC.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>[CH:7]1([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:24]3[C:25]([NH2:30])=[N:26][CH:27]=[CH:28][N:29]=3)=[CH:16][CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2762242-Amino-3-chloropyrazineHCID 222898184-Cyclohexyloxy-benzeneboronic acid

Product 1

HCID 667481483-[4-(Cyclohexyloxy)phenyl]pyrazin-2-amineYield 77.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of sodium carbonate (491 mg), tetrakis(triphenylphosphine)palladium(0) (80 mg), 4-(cyclohexyloxy)phenylboronic acid (612 mg) and 3-chloropyrazin-2-amine (300 mg) in water (3 mL) and DME (15 mL) was stirred at 80° C. for 4 hr. Silica gel was added and the mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give 3-[4-(cyclohexyloxy)phenyl]pyrazin-2-amine (485 mg) as a white solid.

Workup

  1. additionSilica gel was added
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record
ord-8a70dacd0aaf4b178e7fa8e553645357
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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