Ethanol → HCID 90402443, compound

HRID 2200744Notes

Reaction equation

HRID 2200744 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH2:19][OH:20])[C:12](=[O:21])[N:11]([CH3:22])[C:10]=3[N:9]=[C:8]2[CH2:23][C:24]([OH:26])=[O:25])=[CH:4][CH:3]=1.[CH2:29](O)[CH3:30]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH2:19][OH:20])[C:12](=[O:21])[N:11]([CH3:22])[C:10]=3[N:9]=[C:8]2[CH2:23][C:24]([O:26][CH2:29][CH3:30])=[O:25])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 90402854HCID 90402854, compound

Product 1

HCID 90402443HCID 90402443, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

Step 3 Crude 2-(7-(4-chlorobenzyl)-1-(3-hydroxypropyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)acetic acid (0.14 g, 0.36 mmol) was dissolved in ethanol (5 mL) and concentrated sulfuric acid (1 drop). The reaction was heated at reflux for 1 h. The reaction was cooled, evaporated under reduced pressure to remove the ethanol then diluted with water (50 mL) and extracted with ethyl acetate (3×40 mL). The combined extracts were dried with magnesium sulfate, filtered and the solvent was removed under reduced pressure to a light golden oil. The oil was purified using a 12 g silica gel flash column and eluted with 20% ethyl acetate/hexanes to give ethyl 2-(7-(4-chlorobenzyl)-1-(3-hydroxypropyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)acetate (0.062, 40% yield) as a light tan solid. LCMS retention time=2.804 min and 99% purity, LCMS MH+ 435. 1H NMR (CDCl3) δ 7.21 (dd, 4H, J=8 Hz and 84 Hz), 5.57 (s, 2H), 4.11-4.23 (m, 4H), 3.77 (s, 2H), 3.59 (s, 3H), 3.50-3.56 (m, 2H), 3.32-3.39 (m, 1H), 1.86-1.94 (m, 2H), 1.25 (t, 3H, J=8 Hz).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 1 h
  3. temperatureThe reaction was cooled
  4. customevaporated under reduced pressure
  5. customto remove the ethanol
  6. additionthen diluted with water (50 mL)
  7. extractionextracted with ethyl acetate (3×40 mL)
  8. dry with materialThe combined extracts were dried with magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent was removed under reduced pressure to a light golden oil
  11. customThe oil was purified
  12. washeluted with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-c42fff347c6143b3a8b423155dd242ed
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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