Isopropyl iodide → 5-Iodo-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 82176Notes

Reaction equation

HRID 82176 reaction equation
[I:1][C:2]1[C:10]2[CH:9]=[N:8][CH:7]=[N:6][C:5]=2[NH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH:18]([CH3:20])[CH3:19].[Cl-].[NH4+]>CN(C=O)C>[I:1][C:2]1[C:10]2[CH:9]=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH:18]([CH3:20])[CH3:19])[CH:3]=1

Participants

6

Reactant 4

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 106103365-Iodo-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 708171765-Iodo-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidineYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-iodo-7H-pyrrolo[2,3-d]pyrimidine (Preparation 201, 2.90 g, 12.0 mmol) and cesium carbonate (5.78 g, 17.8 mmol) in DMF (45 mL) was added 2-iodopropane (1.78 mL, 17.8 mmol). The mixture was stirred at room temperature for 3 hours. The reaction mixture was then poured onto saturated aqueous ammonium chloride (500 mL) and a solid precipitated. The solid was collected by filtration, rinsed with water (200 mL) and dried under reduced pressure for 17 hours to afford the title compound as a brown solid in 77% yield, 2.61 g.

Workup

  1. customa solid precipitated
  2. filtrationThe solid was collected by filtration
  3. washrinsed with water (200 mL)
  4. customdried under reduced pressure for 17 hours

Sources & evidence

ORD record
ord-62c92f0c8c86496cb5550895e0d2c83d
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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