Sodium Thiosulfate → 5-[2-(2-bromo-phenyl)-1-tert-butyl-1H-benzimidazol-5-yl]-pyrimidin-2-ylamine

HRID 1966676Notes

Reaction equation

HRID 1966676 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([NH2:19])[C:11]([NH:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:12][CH:13]=2)=[CH:4][N:3]=1.[Br:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=O.OOS([O-])=O.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C.O>[Br:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[C:23]1[N:14]([C:15]([CH3:16])([CH3:18])[CH3:17])[C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:4]=[N:3][C:2]([NH2:1])=[N:7][CH:6]=3)=[CH:9][C:10]=2[N:19]=1

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 811292-BromobenzaldehydeHCID 23707502Potassium hydroxy sulfiteHCID 585418994-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine

Product 1

HCID 585419535-[2-(2-bromo-phenyl)-1-tert-butyl-1H-benzimidazol-5-yl]-pyrimidin-2-ylamineYield 48.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine (1 g, 3.89 mmol) in DMF (30 mL) is added 2-bromobenzaldehyde (0.7 mL, 5.83 mmol) at room temperature. Oxone (2.4 g, 3.89 mmol) in H2O (5 mL) is added and the solution is stirred for 1 hour. Saturated sodium thiosulfate solution (10 mL) is added and the mixture is extracted with EtOAc (3×15 mL) and H2O (20 mL). The combined organic layer is dried (MgSO4), filtered and concentrated. The residue is purified by silica gel flash column chromatography eluting with 10% MeOH in CH2Cl2 to afford 5-[2-(2-bromo-phenyl)-1-tert-butyl-1H-benzimidazol-5-yl]-pyrimidin-2-ylamine (800 mg, 48%) as a white solid.

Workup

  1. extractionthe mixture is extracted with EtOAc (3×15 mL) and H2O (20 mL)
  2. dry with materialThe combined organic layer is dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel flash column chromatography
  6. washeluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-9d134a8aa29a4217be9d88cb80825551
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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