Potassium Iodide → Methyl 2-(2-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-methylpropanoate

HRID 82157Notes

Reaction equation

HRID 82157 reaction equation
Br[C:2]([CH3:8])([CH3:7])[C:3]([O:5][CH3:6])=[O:4].[Cl:9][C:10]1[N:11]=[CH:12][C:13]2[C:18]([I:19])=[CH:17][NH:16][C:14]=2[N:15]=1.[I-].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[Cl:9][C:10]1[N:11]=[CH:12][C:13]2[C:18]([I:19])=[CH:17][N:16]([C:2]([CH3:8])([CH3:7])[C:3]([O:5][CH3:6])=[O:4])[C:14]=2[N:15]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 90097Methyl 2-bromo-2-methylpropionateHCID 529112452-chloro-5-iodo-7H-pyrrolo(2,3-d)pyrimidine

Product 1

HCID 86672082Methyl 2-(2-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-methylpropanoateYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 2-bromo-2-methylpropanoate (663 mL, 5.13 mmol) was added to 2-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (358.1 g, 1.28 mol) (see Preparation 40), potassium iodide (21.3 g, 128 mmol) and cesium carbonate (1670 g, 5.13 mol) in DMF (7162 mL). The mixture was heated at 60° C. for 19 hours. The reaction mixture was diluted with water (7000 mL) and stirred at room temperature for 42 hours. The mixture was filtered and the solid was washed with water (500 mL) to afford the title compound as a beige solid in 92% yield, 445.8 g.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with water (500 mL)

Sources & evidence

ORD record
ord-92d6520beac845d689dece6a6e341f5a
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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