Ethanol → 7-benzyl-8-ethoxy-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione

HRID 2200565Notes

Reaction equation

HRID 2200565 reaction equation
[Na].[CH2:2]([N:9]1[C:17]2[C:16](=[O:18])[N:15]([CH2:19][CH2:20][CH2:21][OH:22])[C:14](=[O:23])[N:13]([CH2:24][CH3:25])[C:12]=2[N:11]=[C:10]1Cl)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:27]([OH:29])[CH3:28]>>[CH2:2]([N:9]1[C:17]2[C:16](=[O:18])[N:15]([CH2:19][CH2:20][CH2:21][OH:22])[C:14](=[O:23])[N:13]([CH2:24][CH3:25])[C:12]=2[N:11]=[C:10]1[O:29][CH2:27][CH3:28])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 5360545Sodium2×HCID 904030297-benzyl-8-chloro-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 904023587-benzyl-8-ethoxy-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dioneYield 77.9%

Conditions

Temperature
40 °C

Procedure

A solution of sodium (50 mg, 2.17 mmol) in ethyl alcohol (10 mL) was stirred at 40° C. under nitrogen until the sodium was consumed. Then 7-benzyl-8-chloro-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione (150 mg, 0.414 mmol) was added at 0° C. and the mixture was stirred at 40° C. for 4 h. The mixture was quenched with ice-water (15 mL) and concentrated. The aqueous residue was extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered and concentrated to give 7-benzyl-8-ethoxy-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione (120 mg, 77.9% yield) as yellow solid. LCMS retention time 1.488 min; LCMS MH+ 373.

Workup

  1. customwas consumed
  2. customThe mixture was quenched with ice-water (15 mL)
  3. concentrationconcentrated
  4. extractionThe aqueous residue was extracted with ethyl acetate
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8349567f587a4b4d8b239239ba093543
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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