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

HRID 1909916Notes

Reaction equation

HRID 1909916 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][NH:5][C:4]2=[N:8][CH:9]=[CH:10][C:3]=12.[H-].[Na+].I[CH3:14]>CN(C)C=O>[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([CH3:14])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178418725HCID 178418725, compound

Product 1

HCID 2658294-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidineYield 73.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 4-chloro-1H-pyrrolo[2,3-d]pyrimidine (15.2 g, 99 mmol) in N,N-Dimethylformamide (DMF) (100 mL) at 0 C was added 60% NaH (5.15 g, 129 mmol) portionwise. After H2 bubbling stopped, iodomethane (6.81 mL, 109 mmol) was added dropwise, and then the reaction mixture was allowed to warm to room temperature. After 3 hours, the reaction mixture was poured slowly onto water (˜800 mL; Caution: H2 evolution due to quenching excess NaH). The resulting solid was filtered and washed with water followed by hexanes to afford 4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (12.2 g) as an off-white solid.

Workup

  1. additionthe reaction mixture was poured slowly onto water (˜800 mL; Caution: H2 evolution due to quenching excess NaH)
  2. filtrationThe resulting solid was filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-5185f755a4f0440dae89e0a6eb295537
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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