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

HRID 1051482Notes

Reaction equation

HRID 1051482 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:5]=[CH:6][C:7]2[CH:12]=[CH:11][NH:10][C:8]=2[N:9]=1.[CH3:13]I>C1COCC1.O>[Cl:3][C:4]1[N:5]=[CH:6][C:7]2[CH:12]=[CH:11][N:10]([CH3:13])[C:8]=2[N:9]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57067742-Chloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 574158882-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidineYield 59.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of NaH (106.6 mg, 2.67 mmol) in THF (5 mL) was added 2-chloro-7H-pyrrolo[2,3-d]pyrimidine (500 mg, 2.54 mmol) at 0° C. and stirred for 30 minutes at the same temperature. CH3I (1.5 g, 10.2 mmol) was added at 0° C. and the combined mixture stirred for 3 h at 15° C. After TLC showed the reaction was complete, the mixture was diluted with water 20 mL) and extracted with ethyl acetate EA (2×20 mL) and the combined organic layers were washed with brine (30 mL), dried over Na2SO4 and concentrated to give the title compound (254 mg, 47.4%) as colorless oil which was used in next step without further purification.

Workup

  1. stirringthe combined mixture stirred for 3 h at 15° C
  2. extractionextracted with ethyl acetate EA (2×20 mL)
  3. washthe combined organic layers were washed with brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d4f396a6a4cd462b933d766abc1c53cb
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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