m-Toluidine → HCID 68205817, compound

HRID 333532Notes

Reaction equation

HRID 333532 reaction equation
Cl[C:2]1[C:3]([NH:8][CH:9]([CH3:11])[CH3:10])=[N:4][CH:5]=[CH:6][N:7]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:9]([NH:8][C:3]1[C:2]([NH:12][C:13]2[CH:14]=[C:15]([CH3:19])[CH:16]=[CH:17][CH:18]=2)=[N:7][CH:6]=[CH:5][N:4]=1)([CH3:11])[CH3:10]

Participants

7

Reactant 3

HCID 7934m-ToluidineHCID 214776373-Chloro-N-(propan-2-yl)pyrazin-2-amineHCID 23676156Sodium t-butoxide

Product 1

HCID 68205817HCID 68205817, compoundYield 87.3%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

3-chloro-N-isopropylpyrazin-2-amine (6 g, 35.0 mmol), m-toluidine (5.62 g, 52.4 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (0.435 g, 0.699 mmol), Pd2(dba)3 (0.320 g, 0.350 mmol), and sodium t-butoxide (5.04 g, 52.4 mmol) were mixed in 200 mL of toluene and degassed for 20 minutes. The mixture was heated to reflux for 5 h. The reaction was cooled to room temperature and water was added. The reaction mixture was extracted with dichloromethane and washed with water. The crude was columned with 10% ethyl acetate and dichloromethane to give N2-isopropyl-N3-(m-tolyl)pyrazine-2,3-diamine (7.4 g, 87%).

Workup

  1. customdegassed for 20 minutes
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 5 h
  4. additionwater was added
  5. extractionThe reaction mixture was extracted with dichloromethane
  6. washwashed with water

Sources & evidence

ORD record
ord-7b43fcefbd064fe48b84b75d106b9eab
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

Loading…