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

HRID 1869178Notes

Reaction equation

HRID 1869178 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:9]=[CH:8][NH:7][C:6]2=[N:10][CH:11]=[CH:12][C:5]=12.CI.[C:15](OCC)(=O)C>CN(C)C=O.O>[Cl:3][C:4]1[C:5]2[CH:12]=[CH:11][N:10]([CH3:15])[C:6]=2[N:7]=[CH:8][N:9]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 178418725HCID 178418725, compound

Product 1

HCID 2658294-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
20 °C

Procedure

0.4 g (12.5 mmol) of sodium hydride is added to 25 cm3 of dimethylformamide under an argon atmosphere at a temperature in the region of 20° C., and a solution of 1.8 g (11.7 mmol) of 4-chloropyrrolo[2,3-d]pyrimidine in 25 cm3 of dimethylformamide is then added dropwise over the course of 15 minutes. The reaction mixture is stirred at a temperature in the region of 20° C. for 1 hour, 1.12 cm3 (18 mmol) of methyl iodide are then added, and stirring is continued for 15 hours at a temperature in the region of 20° C. The reaction mixture is then poured into a mixture of 200 cm3 of ethyl acetate and 200 cm3 of water. The organic phase is separated out after the phases have settled, washed successively twice with 200 cm3 of water and 200 cm3 of saturated aqueous sodium chloride solution, dried over magnesium sulphate and then concentrated to dryness under reduced pressure (2.7 kPa), giving 1.35 g of 4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine in the form of a brown powder. Mass spectrum (DCI): m/e 168 (MH+) (base peak).

Workup

  1. stirringstirring
  2. waitis continued for 15 hours at a temperature in the region of 20° C
  3. customThe organic phase is separated out after the phases
  4. washwashed successively twice with 200 cm3 of water and 200 cm3 of saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-cb603d1972d6481389b6f19530128fef
Source dataset
uspto-grants-2009_12
Patent number
US07638521B2

Reaction notes

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