2-Bromopropane → 4-Chloro-5-iodo-7-(propan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 611530Notes

Reaction equation

HRID 611530 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][NH:5][C:4]2=[N:8][CH:9]=[C:10]([I:11])[C:3]=12.[H-].[Na+].[H][H].[CH:16](Br)([CH3:18])[CH3:17]>CN(C)C=O>[Cl:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([CH:16]([CH3:18])[CH3:17])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compoundHCID 178478409HCID 178478409, compound

Product 1

HCID 195974264-Chloro-5-iodo-7-(propan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-Chloro-5-iodo-pyrrolo[2,3-d]-pyrimidine (5.0 g) was added under nitrogen to a mixture of sodium hydride (0.8 g of a 60% dispersion in mineral oil) in N,N-dimethylformamide (100 ml) at 0° C. and then the mixture was allowed to warm to ambient temperature. When hydrogen evolution had ceased a solution of isopropyl bromide (17 ml) in N,N-dimethylformamide (50 ml) was added dropwise. The mixture was stirred for 20 hours at ambient temperature and then quenched with water (150 ml). The mixture was extracted with ethyl acetate to give 4-chloro-5-iodo-7-isopropylpyrrolo[2,3-d]pyrimidine.

Workup

  1. additionwas added dropwise
  2. customquenched with water (150 ml)
  3. extractionThe mixture was extracted with ethyl acetate

Sources & evidence

ORD record
ord-abae33a3bfce47f9a8aaea342bdafa9b
Source dataset
uspto-grants-1999_12
Patent number
US06001839

Reaction notes

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