Methyl iodide → 6-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-D]pyrimidine

HRID 851908

Reaction equation

HRID 851908 reaction equation
[Br:1][C:2]1[NH:11][C:5]2[N:6]=[CH:7][N:8]=[C:9]([Cl:10])[C:4]=2[CH:3]=1.[H-].[Na+].[CH3:14]I>C1COCC1>[Br:1][C:2]1[N:11]([CH3:14])[C:5]2[N:6]=[CH:7][N:8]=[C:9]([Cl:10])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 457898276-Bromo-4-chloro-7H-pyrrolo[2,3-D]pyrimidine

Product 1

HCID 589283276-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-D]pyrimidineYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (122 mg, 0.53 mmol), prepared as in reference 1, in THF (5 mL) at 0° C. is added NaH (31.8 mg, 0.80 mmol, 60% dispersion in oil) portion wise and the reaction mixture is warmed to room temperature for 1 hour. Methyl iodide (103 μL, 1.59 mmol) is added and the mixture is stirred overnight. The reaction is quenched with water and extracted three times with EtOAc. The combined organic layer is washed with brine, dried over MgSO4, and concentrated. Flash column chromatography of the crude product using 1% MeOH in DCM yielded 100 mg of 6-bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (77%); 1H NMR (500 MHz, DMSO) δ 8.64 (s, 1H), 6.96 (s, 1H), 3.79 (s, 3H); LC-ESMS observed [M+H]+ 245.9 (calculated for C7H5BrClN3 244.9).

Workup

  1. customThe reaction is quenched with water
  2. extractionextracted three times with EtOAc
  3. washThe combined organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d46715d983734042aa618886ba717c99
Source dataset
uspto-grants-2007_08
Patent number
US07253166B2

Linked notes

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