Potassium Carbonate → 7-(2,2-dimethyl-propyl)-6-(3-nitro-[1,2,4]triazol-1-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

HRID 271555Notes

Reaction equation

HRID 271555 reaction equation
Br[CH2:2][C:3]1[N:13]([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:6]2[N:7]=[C:8]([C:11]#[N:12])[N:9]=[CH:10][C:5]=2[CH:4]=1.[N+:19]([C:22]1[N:26]=[CH:25][NH:24][N:23]=1)([O-:21])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[CH3:16][C:15]([CH3:18])([CH3:17])[CH2:14][N:13]1[C:6]2[N:7]=[C:8]([C:11]#[N:12])[N:9]=[CH:10][C:5]=2[CH:4]=[C:3]1[CH2:2][N:24]1[CH:25]=[N:26][C:22]([N+:19]([O-:21])=[O:20])=[N:23]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 113128256-Bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrileHCID 178526901HCID 178526901, compound

Product 1

HCID 101320297-(2,2-dimethyl-propyl)-6-(3-nitro-[1,2,4]triazol-1-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrileYield 41%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

6-Bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (3 mmol) and 3-nitro-[1,2,4]triazole (3 mmol) are dissolved in DMSO (20 ml). Potassium carbonate (6 mmol) is added to the solution. The mixture is allowed to stir at room temperature overnight. The reaction mixture is diluted with H2O and extracted with AcOEt. The organic layer is dried over MgSO4 and evaporated in vacuo. The residue is purified by silica gel column chromatography (n-hexane:AcOEt=1:5) to give 7-(2,2-dimethyl-propyl)-6-(3-nitro-[1,2,4]triazol-1-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 41% yield.

Workup

  1. extractionextracted with AcOEt
  2. dry with materialThe organic layer is dried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue is purified by silica gel column chromatography (n-hexane:AcOEt=1:5)

Sources & evidence

ORD record
ord-8dbb49de1d744a5a8f92b641824f2e38
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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