N,N'-Dimethylethylenediamine → 5-[1-tert-Butyl-2-(5-methanesulfonyl-2-[1,2,4]triazol-1-yl-phenyl)-1H-benzoimidazol-5-yl]-pyrimidin-2-ylamine

HRID 1966794Notes

Reaction equation

HRID 1966794 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N:28]2[CH:32]=[N:31][CH:30]=[N:29]2)=[C:6]([C:8]2[N:12]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:11]3[CH:17]=[CH:18][C:19]([C:21]4[CH:22]=[N:23][C:24]([NH2:27])=[N:25][CH:26]=4)=[CH:20][C:10]=3[N:9]=2)[CH:7]=1.[Na+].[CH3:34][S:35]([O-:37])=[O:36].CNCCNC>CS(C)=O.CCOC(C)=O.O.FC(F)(F)S([O-])(=O)=O.[Cu+2].FC(F)(F)S([O-])(=O)=O>[C:13]([N:12]1[C:11]2[CH:17]=[CH:18][C:19]([C:21]3[CH:26]=[N:25][C:24]([NH2:27])=[N:23][CH:22]=3)=[CH:20][C:10]=2[N:9]=[C:8]1[C:6]1[CH:7]=[C:2]([S:35]([CH3:34])(=[O:37])=[O:36])[CH:3]=[CH:4][C:5]=1[N:28]1[CH:32]=[N:31][CH:30]=[N:29]1)([CH3:15])([CH3:14])[CH3:16]

Participants

8

Reactant 3

HCID 8070N,N'-DimethylethylenediamineHCID 2733271Sodium methanesulfinateHCID 585418955-[2-(5-Bromo-2-1,2,4-triazol-1-yl-phenyl)-1-tert-butyl-1H-benzimidazol-5-yl]-pyrimidin-2-ylamine

Product 1

HCID 532382985-[1-tert-Butyl-2-(5-methanesulfonyl-2-[1,2,4]triazol-1-yl-phenyl)-1H-benzoimidazol-5-yl]-pyrimidin-2-ylamineYield 99.4%

Reagents, catalysts & solvents 4

HCID 2734996copper(II) trifluoromethanesulfonateCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a microwave vial is added 5-[2-(5-bromo-2-[1,2,4]triazol-1-yl-phenyl)-1-tert-butyl-1H-benzoimidazol-5-yl]-pyrimidin-2-ylamine (example 6) (237 mg, 0.48 mmol) in DMSO (10 mL), followed by the addition of methanesulfinic acid sodium salt (123 mg, 0.96 mmol), copper(II) trifluoromethanesulphonate (175 mg, 0.48 mmol) and N,N′-dimethylethylenediamine (85 mg, 0.96 mmol). The reaction mixture is heated in microwave reactor at 120° C. for 1.5 hours. The reaction mixture is diluted with EtOAc (20 mL) and water (10 mL). The organic layer is separated, washed with brine (10 mL), dried under anhydrous Na2SO4 (500 mg). The mixture is filtered and concentrated. The residue is purified by silica gel flash chromatography with 0-8% MeOH/CH2Cl2 as the eluent. The product fractions are collected and concentrated to afford the title compound (233 mg, 99%). LCMS (ESMS): m/z 489.52 (M++1)

Workup

  1. customThe organic layer is separated
  2. washwashed with brine (10 mL)
  3. customdried under anhydrous Na2SO4 (500 mg)
  4. filtrationThe mixture is filtered
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel flash chromatography with 0-8% MeOH/CH2Cl2 as the eluent
  7. customThe product fractions are collected
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b4eb9f6d248d4725aa11d5d2a8900cd8
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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