Iodoethane → 4-Chloro-7-ethyl-2-(methylthio)-7H-pyrrolo[2,3-d]pyrimidine

HRID 2116461Notes

Reaction equation

HRID 2116461 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5]2[CH:14]=[CH:13][NH:12][C:6]=2[N:7]=[C:8]([S:10][CH3:11])[N:9]=1.[CH2:15](I)[CH3:16]>CN(C)C=O>[Cl:3][C:4]1[C:5]2[CH:14]=[CH:13][N:12]([CH2:15][CH3:16])[C:6]=2[N:7]=[C:8]([S:10][CH3:11])[N:9]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 53244144-chloro-2-(methylthio)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 859081894-Chloro-7-ethyl-2-(methylthio)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.44 g, 60% dispersion in oil) was added portionwise to a stirred solution of 4-chloro-2-(methylthio)-7H-pyrrolo[2,3-d]pyrimidine (2 g) in N,N-dimethylformamide (30 ml) at 0° C. After 0.75 h, ethyl iodide (0.88 ml) was added, the mixture stirred for 2 h, quenched with water and partitioned between ethyl acetate and brine. The organics were washed with water, dried (MgSO4), evaporated under reduced pressure and the residue purified by chromatography on silica eluting with 15% ethyl acetate in isohexane. Yield 1.98 g

Workup

  1. customquenched with water
  2. custompartitioned between ethyl acetate and brine
  3. washThe organics were washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customthe residue purified by chromatography on silica eluting with 15% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-863f109b2823438793626974aaa0fe92
Source dataset
uspto-grants-2008_10
Patent number
US07439240B2

Reaction notes

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