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

HRID 1966751Notes

Reaction equation

HRID 1966751 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.[I: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.CCOC(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:23]1[C:22]1[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=1[I:20])([CH3:16])([CH3:18])[CH3:17]

Participants

8

Reactant 4

HCID 24477Sodium ThiosulfateHCID 6434392-IodobenzaldehydeHCID 23707502Potassium hydroxy sulfiteHCID 585418994-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine

Product 1

HCID 585420695-[1-tert-butyl-2-(2-iodo-phenyl)-1H-benzimidazol-5-yl]-pyrimidin-2-ylamineYield 34.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask are added 4-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine (430 mg, 1.67 mmol) in DMF (10 mL) and water (3 mL), followed by the addition of 2-iodobenzaldehyde (445 mg, 1.92 mmol) and oxone (1180 mg, 1.92 mmol). The reaction mixture is stirred at room temperature for 1 hour. Saturated sodium thiosulfate (10 mL) is added. The reaction mixture is diluted with EtOAc (50 mL). The organic layer is washed with water, brine, dried under anhydrous Na2SO4, filtered and concentrated. The residue is purified by silica gel flash column chromatography with 0-5% MeOH/CH2Cl2 as the eluent. The product fractions are collected and concentrated to afford 5-[1-tert-butyl-2-(2-iodo-phenyl)-1H-benzimidazol-5-yl]-pyrimidin-2-ylamine (270 mg, 34%) as a light brown solid. LCMS (ESMS): m/z 470.58 (M++1)

Workup

  1. washThe organic layer is washed with water, brine
  2. customdried under anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel flash column chromatography with 0-5% MeOH/CH2Cl2 as the eluent
  6. customThe product fractions are collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1049636580904e4f9ba24c3da58b45c1
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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