Water → HCID 58485736, compound

HRID 1396142Notes

Reaction equation

HRID 1396142 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:7]2[CH:14]=[CH:13][NH:12][C:8]=2[N:9]=[CH:10][N:11]=1.CN(C)C=O.[I:20]N1C(=O)CCC1=O.O>ClCCl>[I:20][C:14]1[C:7]2[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[N:11][CH:10]=[N:9][C:8]=2[NH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 120273N-IodosuccinimideHCID 58485838HCID 58485838, compound

Product 1

HCID 58485736HCID 58485736, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-(2-methoxy-ethoxy)-7H-pyrrolo[2,3-d]pyrimidine (24, 5.70 g, 29.5 mmol) in 150.0 mL of dichloromethane, N,N-dimethylformamide (6.0 mL, 78 mmol) and N-iodosuccinimide (7.22 g, 32.1 mmol) are added and the reaction stirred at room temperature for 2 hours. The reaction is poured into water and extracted with ethyl acetate. The organic layer is dried with sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is washed with ethyl acetate and hexane to provide the desired compound (25, 6.75 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer is dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. washThe resulting material is washed with ethyl acetate and hexane

Sources & evidence

ORD record
ord-ab5f920cb0b548d5ac29a43a85b3102b
Source dataset
uspto-grants-2014_12
Patent number
US08901118B2

Reaction notes

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