Isopropyl iodide → 4-Chloro-7-isopropyl-7H-pyrrolo[2,3-D]pyrimidine

HRID 736332Notes

Reaction equation

HRID 736332 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[Cl:7][C:8]1[C:9]2[CH:16]=[CH:15][NH:14][C:10]=2[N:11]=[CH:12][N:13]=1.I[CH:18]([CH3:20])[CH3:19]>CN(C=O)C>[Cl:7][C:8]1[C:9]2[CH:16]=[CH:15][N:14]([CH:18]([CH3:20])[CH3:19])[C:10]=2[N:11]=[CH:12][N:13]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 722073574-Chloro-7-isopropyl-7H-pyrrolo[2,3-D]pyrimidineYield 98.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cs2CO3 (382 g, 1.2 mol) was added to a solution of 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine (120 g, 0.78 mol) in DMF (1.0 L) at room temperature. The resulting mixture was stirred for 30 min. 2-Iodopropane (267 g, 1.6 mol) was added and the reaction and stirred for 5 h at room temperature. The reaction mixture was filtered and the solid was washed with EtOAc (3×500 mL). The combined filtrates were washed with water (3×500 mL) and brine (3×250 mL), dried (Na2SO4), filtered, and concentrated in vacuo to afford the title compound as a yellow solid (151 g, 94%). MS: 19.6 (MH+); HPLC Rf: 4.89 min. (HPLC method 4).

Workup

  1. customthe reaction
  2. stirringstirred for 5 h at room temperature
  3. filtrationThe reaction mixture was filtered
  4. washthe solid was washed with EtOAc (3×500 mL)
  5. washThe combined filtrates were washed with water (3×500 mL) and brine (3×250 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-85e23e59b5014fdb9b6cd78595d85109
Source dataset
uspto-grants-2009_09
Patent number
US07595325B2

Reaction notes

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