Sodium Thiosulfate → 5-[1-tert-Butyl-2-(5-methoxy-2-1,2,4-triazol-1-yl-phenyl)-1H-benzimidazol-5-yl]-pyrimidin-2-ylamine

HRID 1966671Notes

Reaction equation

HRID 1966671 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.[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([N:30]2[CH:34]=[N:33][CH:32]=[N:31]2)=[C:26]([CH:29]=1)[CH:27]=O.OOS([O-])=O.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C.O>[C:15]([N:14]1[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]=[C:27]1[C:26]1[CH:29]=[C:22]([O:21][CH3:20])[CH:23]=[CH:24][C:25]=1[N:30]1[CH:34]=[N:33][CH:32]=[N:31]1)([CH3:16])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 23707502Potassium hydroxy sulfiteHCID 58541892HCID 58541892, compoundHCID 585418994-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine

Product 1

HCID 532364935-[1-tert-Butyl-2-(5-methoxy-2-1,2,4-triazol-1-yl-phenyl)-1H-benzimidazol-5-yl]-pyrimidin-2-ylamineYield 48%

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 (50 mg, 0.194 mmol) in DMF (10 mL) is added 5-methoxy-2-1,2,4-triazol-1-yl-benzaldehyde (47 mg, 0.233 mmol) at room temperature. Oxone (119 mg, 0.194 mmol) in H2O (2 mL) is added and the solution is stirred for 1 hour. Saturated sodium thiosulfate solution (5 mL) is added and the mixture is extracted with EtOAc (3×10 mL) and H2O (10 mL). The combined organic layer is dried with MgSO4, filtered and concentrated. The residue is purified by silica gel flash column chromatography eluting with 10% MeOH in CH2Cl2 to afford the title compound (41 mg, 47%) as a pale brown solid. LCMS (ESMS): m/z 441.20 (M++1).

Workup

  1. extractionthe mixture is extracted with EtOAc (3×10 mL) and H2O (10 mL)
  2. dry with materialThe combined organic layer is dried with 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-620ab9d3b0db4d2d8e40d4c27c2a593c
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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