Dibutyltin oxide → 5-{1-tert-Butyl-2-[5-(2H-tetrazol-5-yl)-2-[1,2,4]triazol-1-yl-phenyl]-1H-benzoimidazol-5-yl}-pyrimidin-2-ylamine

HRID 1966781Notes

Reaction equation

HRID 1966781 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:33]=[CH:32][C:11]3[N:12]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:13]([C:15]4[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=4[N:23]4[CH:27]=[N:26][CH:25]=[N:24]4)[C:18]#[N:19])=[N:14][C:10]=3[CH:9]=2)=[CH:4][N:3]=1.[N:34]([Si](C)(C)C)=[N+:35]=[N-:36].C([Sn](=O)CCCC)CCC>CN(C=O)C>[C:28]([N:12]1[C:11]2[CH:32]=[CH:33][C:8]([C:5]3[CH:6]=[N:7][C:2]([NH2:1])=[N:3][CH:4]=3)=[CH:9][C:10]=2[N:14]=[C:13]1[C:15]1[CH:16]=[C:17]([C:18]2[N:34]=[N:35][NH:36][N:19]=2)[CH:20]=[CH:21][C:22]=1[N:23]1[CH:27]=[N:26][CH:25]=[N:24]1)([CH3:29])([CH3:30])[CH3:31]

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 532376053-[5-(2-Amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-4-1,2,4-triazol-1-yl-benzonitrile

Product 1

HCID 532382995-{1-tert-Butyl-2-[5-(2H-tetrazol-5-yl)-2-[1,2,4]triazol-1-yl-phenyl]-1H-benzoimidazol-5-yl}-pyrimidin-2-ylamineYield 9.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-[5-(2-Amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-4-1,2,4-triazol-1-yl-benzonitrile (example 7) (100 mg, 0.23 mmol) in DMF (5 mL) are added azidotrimethylsilane (0.06 mL, 0.46 mmol) and dibutyltin oxide (175 mg, 0.69 mmol) at room temperature. The solution is heated up to 100° C. for 5 hours in a microwave reactor. The solution is cooled down and is extracted with Sat. NH4Cl (10 mL) and EtOAc (3×10 mL). The combined organic layer is dried with MgSO4 (500 mg) and is filtered. The filtrate is concentrated and the residue is purified by preparative HPLC to afford the title compound (10 mg, 9%) LCMS (ESMS): m/z: 479.40 (M++1).

Workup

  1. temperatureThe solution is cooled down
  2. extractionis extracted with Sat. NH4Cl (10 mL) and EtOAc (3×10 mL)
  3. dry with materialThe combined organic layer is dried with MgSO4 (500 mg)
  4. filtrationis filtered
  5. concentrationThe filtrate is concentrated
  6. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-ff8f22cc47954896ab5f66f463e7631e
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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