4,6-Dichloro-5-pyrimidinecarbaldehyde → 2-(4,6-Dichloro-pyrimidin-5-yl)-6-imidazol-1-yl-4-methyl-1H-benzimidazole

HRID 1793715Notes

Reaction equation

HRID 1793715 reaction equation
[N:1]1([C:6]2[CH:11]=[C:10]([NH2:12])[C:9]([NH2:13])=[C:8]([CH3:14])[CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[Cl:15][C:16]1[C:21]([CH:22]=O)=[C:20]([Cl:24])[N:19]=[CH:18][N:17]=1>CO>[Cl:15][C:16]1[C:21]([C:22]2[NH:12][C:10]3[CH:11]=[C:6]([N:1]4[CH:5]=[CH:4][N:3]=[CH:2]4)[CH:7]=[C:8]([CH3:14])[C:9]=3[N:13]=2)=[C:20]([Cl:24])[N:19]=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 8196914,6-Dichloro-5-pyrimidinecarbaldehydeHCID 104199825-Imidazol-1-yl-3-methyl-benzene-1,2-diamine

Product 1

HCID 220211832-(4,6-Dichloro-pyrimidin-5-yl)-6-imidazol-1-yl-4-methyl-1H-benzimidazoleYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 5-imidazol-1-yl-3-methyl-benzene-1,2-diamine (180 mg, 0.96 mmol) in methanol (4 mL) was added a solution of 4,6-dichloro-pyrimidine-5-carbaldehyde (183 mg, 0.96 mmol) in methanol (1 mL). The reaction mixture was stirred at room temperature for 14 h. After concentration, the residue was purified by flash column chromatography (5% methanol/CH2Cl2) to yield the title compound (180 mg, 55%). LCMS (M+H)+ m/z 344 (t=1.31 min.).

Workup

  1. concentrationAfter concentration
  2. customthe residue was purified by flash column chromatography (5% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-2fb724584d8e4136acef0b1feedd5538
Source dataset
uspto-grants-2006_07
Patent number
US07081454B2

Reaction notes

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