Isopropyl iodide → 3-Isopropyl-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

HRID 1291236

Reaction equation

HRID 1291236 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4](=[O:10])[NH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH:17](I)([CH3:19])[CH3:18]>CN(C=O)C>[CH:17]([N:3]1[C:4](=[O:10])[C:5]2[CH:9]=[CH:8][NH:7][C:6]=2[N:1]=[CH:2]1)([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 1354086897-Deazahypoxanthine

Product 1

HCID 189190403-Isopropyl-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

Under argon gas, 7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one (1.0 g) was dissolved in DMF (35 ml) with warming. Then, anhydrous potassium carbonate (1.02 g) and isopropyl iodide (1.1 ml) were added and the mixture was stirred at 55° C. for 13 hours. The insoluble matter was filtered off and the solvent was distilled off under reduced pressure. The residue was purified by flash column chromatography (silica gel; hexane: ethyl acetate=4:1→1:1) to provide the title compound (110 mg). 1 H-NMR (CDCl3) δ: 1.48(6H,d,J=7.OHz), 5.31(1H,m), 6.74(1H,dd,J=2.2&3.4Hz), 6.96(1H,dd,J=2.2&3.4Hz), 7.95(1H,s), 9.20(1H,brs).

Workup

  1. temperaturewith warming
  2. filtrationThe insoluble matter was filtered off
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by flash column chromatography (silica gel; hexane: ethyl acetate=4:1→1:1)

Sources & evidence

ORD record
ord-8f2a1c06a491442d8d9ac05223c6c2ad
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Linked notes

Loading…