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

HRID 1396135Notes

Reaction equation

HRID 1396135 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.[CH2:11]([OH:13])[CH3:12].[OH-].[K+]>>[CH2:11]([O:13][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1)[CH3:12]

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]pyrimidineYield 66.9%

Conditions

Temperature
120 °C

Procedure

4-Chloro-7H-pyrrolo[2,3-d]pyrimidine (9, 300 mg, 1.95 mmol) is combined with 3.00 mL of ethanol (10, 51.4 mmol), then potassium hydroxide (0.226 g, 4.03 mmol) is added. The reaction is heated at 120° C. for 3 hours in a microwave, then extracted with ethyl acetate and aqueous saturated ammonium chloride. The organic layer is washed with brine, dried with magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is recrystallized from methanol to provide the desired compound (11, 213 mg). MS (ESI) [M+H+]+=164.9.

Workup

  1. extractionextracted with ethyl acetate and aqueous saturated ammonium chloride
  2. washThe organic layer is washed with brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe resulting material is recrystallized from methanol

Sources & evidence

ORD record
ord-9f8945ba44a84ca1b5f3875d6fc709e1
Source dataset
uspto-grants-2014_12
Patent number
US08901118B2

Reaction notes

Loading…