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

HRID 397400Notes

Reaction equation

HRID 397400 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7]I.[Cl:9][C:10]1[C:11]2[CH:18]=[CH:17][NH:16][C:12]=2[N:13]=[CH:14][N:15]=1.O>CN(C=O)C>[Cl:9][C:10]1[C:11]2[CH:18]=[CH:17][N:16]([CH3:7])[C:12]=2[N:13]=[CH:14][N:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 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 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to Scheme 5, cesium carbonate (968 mg, 3 mmol) followed by methyl iodide (1 g, 7.1 mmol) was added to a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (121 mg, 0.79 mmol) in DMF (5 mL). The mixture was stirred at room temperature for 6 hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried, concentrated and column chromatographed to give 116 mg (88%) of 4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine as a white solid. 1H NMR (360 MHz, DMSO-d6) 8.62 (s, 1H), 7.71 (s, 1H), 6.62 (s, 1H), 3.84 (s, 3H, CH3).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customcolumn chromatographed

Sources & evidence

ORD record
ord-a110dd028d084fa8af55e563f9c61804
Source dataset
uspto-grants-2003_08
Patent number
US06610688B2

Reaction notes

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