Dimethylformamide → 6-(6-Chloro-pyridin-3-yloxymethyl)-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

HRID 271550Notes

Reaction equation

HRID 271550 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.CN(C=O)C.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][N:26]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.O>[Cl:24][C:25]1[N:26]=[CH:27][C:28]([O:31][CH2:2][C:3]2[N:13]([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:6]3[N:7]=[C:8]([C:11]#[N:12])[N:9]=[CH:10][C:5]=3[CH:4]=2)=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 8198212-Chloro-5-hydroxypyridineHCID 113128256-Bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

Product 1

HCID 101089016-(6-Chloro-pyridin-3-yloxymethyl)-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrileYield 99%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

6-Bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (1.3 mmol) is dissolved in DMSO (or DMF) (4 ml). To the solution, 2-chloro-5-hydroxypyridine (1.56 mmol) and K2CO3 (1.69 mmol) are added. The mixture is stirred at room temperature under nitrogen atomosphere for 11 h. The reaction mixture is diluted with water and extracted with AcOEt (twice) and Et2O (twice). The combined organic layer is washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue is purified by silica gel column chromatography (n-hexane:AcOEt=1:1) to give the product in 99% yield.

Workup

  1. extractionextracted with AcOEt (twice) and Et2O (twice)
  2. washThe combined organic layer is washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by silica gel column chromatography (n-hexane:AcOEt=1:1)
  6. customto give the product in 99% yield

Sources & evidence

ORD record
ord-84138099b836413695c26a034c18dcc6
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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