Ethanol → 4-ethoxy-7H-pyrrolo[2,3-d]pyrimidine

HRID 1690037Notes

Reaction equation

HRID 1690037 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[OH-].[K+].[CH2:13]([OH:15])[CH3:14]>>[CH2:13]([O:15][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1)[CH3:14]

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 579632454-ethoxy-7H-pyrrolo[2,3-d]pyrimidine

Procedure

To 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1, 300 mg, 1.95 mmol) in 3.0 mL of ethanol, potassium hydroxide (226 mg, 4.03 mmol) was added and the reaction was microwaved at 120° C. for 3 hours. The reaction was extracted in ethyl acetate and aqueous saturated ammonium chloride. The organic layer was separated and washed with brine, then dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was recrystallized with methanol to provide the desired compound (47, 213 mg). MS (ESI) [M+H+]+=164.9.

Workup

  1. customthe reaction was microwaved at 120° C. for 3 hours
  2. extractionThe reaction was extracted in ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe resulting material was recrystallized with methanol

Sources & evidence

ORD record
ord-f52af7d963fa4cdda4f669ffb041765d
Source dataset
uspto-grants-2012_04
Patent number
US08153641B2

Reaction notes

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