Dimethylformamide → 7-bromo-4-chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine

HRID 532471Notes

Reaction equation

HRID 532471 reaction equation
[Br:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([Cl:11])[C:5]=2[NH:4][CH:3]=1.[CH3:12]N(C)C=O.[H-].[Na+].CI>C(OCC)(=O)C>[Br:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([Cl:11])[C:5]=2[N:4]([CH3:12])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 529876607-bromo-4-chloro-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 722079627-bromo-4-chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To 7-bromo-4-chloro-5H-pyrrolo[3,2-d]pyrimidine (147 mg), N,N-dimethylformamide (10 mL) was added, and NaH (36 mg) was further added thereto, followed by stirring for 30 min. Subsequently, methyl iodide was added thereto, and the reaction mixture was heated to 50° C. and stirred for 2 hours. After completion of the reaction, the reaction mixture was mixed with ethyl acetate and washed with water. The washed mixture was dried over anhydrous sodium sulfate, and filtered and distilled under reduced pressure to obtain the title compound.

Workup

  1. stirringstirred for 2 hours
  2. customAfter completion of the reaction
  3. washwashed with water
  4. dry with materialThe washed mixture was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-f40f16950556459c9b68d8b64f2ae3b1
Source dataset
uspto-grants-2014_10
Patent number
US08853213B2

Reaction notes

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