Potassium Carbonate → 7-(2,2-Dimethyl-propyl)-6-tetrazol-1-ylmethyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

HRID 271556Notes

Reaction equation

HRID 271556 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.[NH:19]1[CH:23]=[N:22][N:21]=[N:20]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.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:19]1[CH:23]=[N:22][N:21]=[N:20]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 113128256-Bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrileHCID 178418441HCID 178418441, compound

Product 1

HCID 598346827-(2,2-Dimethyl-propyl)-6-tetrazol-1-ylmethyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrileYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

6-Bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (0.33 mmol) and 1H-tetrazole (0.65 mmol) are dissolved in DMF (3 ml). To the solution, K2CO3 (0.98 mmol) is added and the mixture is stirred at room temperature under nitrogen atmosphere for 23 h. The reaction mixture is diluted with water and extracted with AcOEt. The organic layer is washed with brine, dried over sodium sulfate, and concentrated. The crude product is purified by silica gel column chromatography to give A in 45% yield and B in 48% yield in the order of elution.

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer is washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product is purified by silica gel column chromatography
  6. customto give A in 45% yield and B in 48% yield
  7. washin the order of elution

Sources & evidence

ORD record
ord-8a274e5c16af4801a716ea3266947218
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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