Sodium Carbonate → 2-Methoxy-4-{6-[(pyridin-3-ylmethyl)amino]pyrazin-2-yl}phenol

HRID 1244397Notes

Reaction equation

HRID 1244397 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[N:4][CH:3]=1.[CH3:16][O:17][C:18]1[CH:23]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:21]=[CH:20][C:19]=1[OH:33].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.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>[CH3:16][O:17][C:18]1[CH:23]=[C:22]([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([NH:8][CH2:9][C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)[N:7]=2)[CH:21]=[CH:20][C:19]=1[OH:33]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27346502-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 219193566-chloro-N-(pyridin-3-ylmethyl)pyrazin-2-amine

Product 1

HCID 1354743192-Methoxy-4-{6-[(pyridin-3-ylmethyl)amino]pyrazin-2-yl}phenolYield 100.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 6-chloro-N-(pyridin-3-ylmethyl)pyrazin-2-amine (49 mg, 0.22 mmol), 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (52 mg, 0.20 mmol), (PPh3)4Pd (23 mg, 0.020 mmol) and a Na2CO3 solution (0.22 mmol of a 2 M solution) in toluene (10 ml) was heated under reflux overnight. After removal of the solvents, the residue was dissolved in CH2Cl2 (150 ml), dried (Na2SO4), filtered and the CH2Cl2 removed in vacuo. The residue was purified by column chromatography, eluting with a n-hexane:ethyl acetate gradient mixture to obtain the desired product (62 mg, 75%).

Workup

  1. temperatureunder reflux overnight
  2. customAfter removal of the solvents
  3. dissolutionthe residue was dissolved in CH2Cl2 (150 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe CH2Cl2 removed in vacuo
  7. customThe residue was purified by column chromatography
  8. washeluting with a n-hexane

Sources & evidence

ORD record
ord-731cb9b51f8341d28a8f9be59a95327f
Source dataset
uspto-grants-2006_10
Patent number
US07122550B2

Reaction notes

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