Water → HCID 19597424, compound

HRID 611543Notes

Reaction equation

HRID 611543 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5]2[C:12]([I:13])=[CH:11][NH:10][C:6]=2[N:7]=[CH:8][N:9]=1.[CH2:14](Br)[CH:15]=[CH2:16].O>CN(C)C=O>[Cl:3][C:4]1[C:5]2[C:12]([I:13])=[CH:11][N:10]([CH2:16][CH:15]=[CH2:14])[C:6]=2[N:7]=[CH:8][N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromide2×HCID 24758Sodium hydrideHCID 148092816-Chloro-7-iodo-7-deazapurine

Product 1

HCID 19597424HCID 19597424, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.28 g of 60% dispersion in mineral oil) was added to a solution of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (1.96 g) in dry N,N-dimethylformamide (40 ml) with stirring under nitrogen at ambient temperature. The mixture was then stirred for 30 minutes and allyl bromide (0.62 ml) was added dropwise. After stirring for 1 hour at ambient temperature more allyl bromide (0.20 ml) was added and the mixture was left stirring at ambient temperature for 18 hours. The mixture was added to water with stirring and the solid which precipitated was collected by filtration and dried to give 4-chloro-5-iodo-7-(prop-1-en-3-yl)-7H-pyrrolo[2,3-d]-pyrimidine which was used directly in b).

Workup

  1. stirringThe mixture was then stirred for 30 minutes
  2. additionwas added
  3. waitthe mixture was left
  4. stirringstirring at ambient temperature for 18 hours
  5. stirringwith stirring
  6. customthe solid which precipitated
  7. filtrationwas collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-4e79fa4271d64ea4b2c26411b015a4af
Source dataset
uspto-grants-1999_12
Patent number
US06001839

Reaction notes

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