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

HRID 1966740Notes

Reaction equation

HRID 1966740 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10]2[CH:11]=[C:12]([NH2:21])[C:13]([NH:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:14][CH:15]=2)=[CH:4][N:3]=1.[N:22]1([C:27]2[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=2[CH:29]=O)[CH:26]=[N:25][CH:24]=[N:23]1.OOS([O-])=O.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C.O.CCOC(C)=O>[C:17]([N:16]1[C:13]2[CH:14]=[CH:15][C:10]([C:5]3[C:6]([O:8][CH3:9])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=3)=[CH:11][C:12]=2[N:21]=[C:29]1[C:28]1[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=1[N:22]1[CH:26]=[N:25][CH:24]=[N:23]1)([CH3:18])([CH3:20])[CH3:19]

Participants

8

Reactant 4

HCID 24477Sodium ThiosulfateHCID 35364462-(1H-1,2,4-Triazol-1-yl)benzaldehydeHCID 23707502Potassium hydroxy sulfiteHCID 585420094-(2-amino-4-methoxy-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine

Product 1

HCID 585419935-[1-tert-Butyl-2-(2-1,2,4-triazol-1-yl-phenyl)-1H-benzimidazol-5-yl]-4-methoxy-pyrimidin-2-ylamineYield 37%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask is added 4-(2-amino-4-methoxy-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine (118 mg, 0.411 mmol) in DMF (4 mL) and water (1 mL), followed by the addition of 2-1,2,4-triazol-1-yl-benzaldehyde (78 mg, 0.45 mmol) and oxone (51 mg, 0.443 mmol). The reaction mixture is stirred at room temperature for 4 hours. Sat. sodium thiosulfate (10 mL) is added. The reaction mixture is diluted with EtOAc. The organic layer is separated, washed with water then brine, dried with Na2SO4, filtered and concentrated. The residue is loaded into a silica gel column. The column is eluted with 0-4% 7M NH3 in MeOH/CH2Cl2. The product fractions are collected and concentrated to afford the title compound (67 mg, 37%) as a light brown solid. LCMS (ESMS): m/z 441.73 (M++1)

Workup

  1. customThe organic layer is separated
  2. washwashed with water
  3. dry with materialbrine, dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washThe column is eluted with 0-4% 7M NH3 in MeOH/CH2Cl2
  7. customThe product fractions are collected
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c4355cb4f04a4de8bc587ca5886a25a9
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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