5-Amino-1-methyl-1H-pyrazole-4-carbonitrile → 4-amino-5-(1H-benzo[d]imidazol-2-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one

HRID 2221048Notes

Reaction equation

HRID 2221048 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]#[N:9].[NH:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[CH2:19][C:20](OCC)=[O:21].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[NH2:9][C:8]1[C:3]2[CH:4]=[N:5][N:6]([CH3:7])[C:2]=2[NH:1][C:20](=[O:21])[C:19]=1[C:11]1[NH:10][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=1

Participants

5

Reactant 3

HCID 2197405-Amino-1-methyl-1H-pyrazole-4-carbonitrileHCID 308071ethyl 2-(1H-1,3-benzodiazol-2-yl)acetateHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 1354961414-amino-5-(1H-benzo[d]imidazol-2-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Amino-1-methyl-1H-pyrazole-4-carbonitrile (1.0 eq) and ethyl 1H-benzimidazol-2-ylacetate (1.0 eq) were dissolved in THF and dried over sieves. LiHMDS (3 eq) was added dropwise and the mixture stirred for 18 hours. The mixture was filtered and diluted with EtOAc, then washed with an aqueous saturated NH4Cl solution. The aqueous layer was washed with EtOAc (3×), and the organic layers combined, dried over MgSO4, and concentrated yielding pure product. LC/MS m/z 281.0 (MH+), Rt 1.41 minutes.

Workup

  1. customdried over sieves
  2. filtrationThe mixture was filtered
  3. additiondiluted with EtOAc
  4. washwashed with an aqueous saturated NH4Cl solution
  5. washThe aqueous layer was washed with EtOAc (3×)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customyielding pure product

Sources & evidence

ORD record
ord-48cab8c2fe094f4ead0d5036b29559fd
Source dataset
uspto-grants-2008_05
Patent number
US07368459B2

Reaction notes

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