Sodium Thiosulfate → 5-{1-tert-Butyl-2-[5-methoxy-2-(5-methyl-thiazol-2-yl)-phenyl]-1H-benzimidazol-5-yl}-pyrimidin-2-ylamine

HRID 1966689Notes

Reaction equation

HRID 1966689 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]([C:30]2[S:31][C:32]([CH3:35])=[CH:33][N:34]=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[C:30]1[S:31][C:32]([CH3:35])=[CH:33][N:34]=1)([CH3:16])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 23707502Potassium hydroxy sulfiteHCID 585418994-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamineHCID 58541979HCID 58541979, compound

Product 1

HCID 532394245-{1-tert-Butyl-2-[5-methoxy-2-(5-methyl-thiazol-2-yl)-phenyl]-1H-benzimidazol-5-yl}-pyrimidin-2-ylamineYield 56.1%

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 (100 mg, 0.39 mmol) in DMF (10 mL) is added 5-methoxy-2-(5-methyl-thiazol-2-yl)-benzaldehyde (99 mg, 0.43 mmol) at room temperature. Oxone (239 mg, 0.39 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 and filtered. The filtrate is concentrated and the residue is purified by silica gel flash column chromatography eluting with 10% MeOH in CH2Cl2 to afford the title compound (103 mg, 56%) as a white solid. LCMS (ESMS): m/z 471.20 (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. concentrationThe filtrate is concentrated
  5. customthe residue is purified by silica gel flash column chromatography
  6. washeluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-b7217b473f0e411fada8a5a4ac07bcfa
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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