Methyl iodide → 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 916778

Reaction equation

HRID 916778 reaction equation
IC.[Cl:3][C:4]1[C:5]2[CH:12]=[CH:11][NH:10][C:6]=2[N:7]=[CH:8][N:9]=1.[C:13](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:3][C:4]1[C:5]2[CH:12]=[CH:11][N:10]([CH3:13])[C:6]=2[N:7]=[CH:8][N:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 2658294-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidineYield 94.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodomethane (12.2 mL, 195 mmol) was added to a solution of 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine (15.0 g, 97.7 mmol) and cesium carbonate (47.7 g, 146.5 mmol) in DMF (200 mL). The reaction mixture was stirred at room temperature 1 h, quenched with H2O (500 mL), and extracted with EtOAc (3×200 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash column chromatography (silica, 2:8→3:7 EtOAc:hexanes) provided the title compound as an off-white solid (15.4 g, 94%). MS: 168.5 (MH+); HPLC Rf: 3.45 min. (HPLC method 4); HPLC purity: 96%.

Workup

  1. customquenched with H2O (500 mL)
  2. extractionextracted with EtOAc (3×200 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography (silica, 2:8→3:7 EtOAc:hexanes)

Sources & evidence

ORD record
ord-2f54b957dd5745c5ae737cef4d7dd066
Source dataset
uspto-grants-2007_09
Patent number
US07271262B2

Linked notes

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