Hydrochloric Acid → HCID 90402381, compound

HRID 2200746Notes

Reaction equation

HRID 2200746 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:20](=[O:21])[C:19]2[N:18]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[C:17]([CH:30]([OH:32])[CH3:31])=[N:16][C:15]=2[N:14]([CH3:33])[C:13]1=[O:34])(C(C)(C)C)(C)C.Cl>C(O)C.O>[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][N:18]2[C:19]3[C:20](=[O:21])[N:12]([CH2:11][CH2:10][CH2:9][OH:8])[C:13](=[O:34])[N:14]([CH3:33])[C:15]=3[N:16]=[C:17]2[CH:30]([OH:32])[CH3:31])=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 904040471-(3-((tert-butyldimethysilyl)oxy)propyl)-7-(4-chlorobenzyl)-8-(1-hydroxyethyl)-3-methyl-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 90402381HCID 90402381, compoundYield 29.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Step 2 1-(3-((tert-butyldimethysilyl)oxy)propyl)-7-(4-chlorobenzyl)-8-(1-hydroxyethyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (0.052 g, 0.10 mmoL) was dissolved in ethanol (2 mL) and 6N aqueous HCl (0.5 mL) was added. The clear solution was stirred at room temperature for 1 h. The reaction was diluted with water (25 mL) and extracted with DCM (3×25 mL). The combined organic extracts were dried with magnesium sulfate, filtered and the solvent removed under reduced pressure to a golden oil. The oil was purified using a 2000 micron preparative TLC plate eluted with 50% ethyl acetate/hexanes. Target band was extracted with ethyl acetate and the solvent was removed under reduced pressure to give 7-(4-chlorobenzyl)-8-(1-hydroxyethyl)-1-(3-hydroxypropyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (0.012 g, 29% yield) as a clear oil. LCMS retention time=2.429 min and 96% purity, LCMS MH+ 393. 1H NMR (CDCl3) δ 7.25 (dd, 4H, J=8 Hz and 64 Hz), 5.65 (dd, J=12 Hz and 40 Hz), 4.91-4.97 (m, 1H), 4.19 (t, 2H, J=4 Hz), 3.61 (s, 3H), 3.51-3.55 (m, 2H), 2.52 (d, 1H, J=4 Hz), 1.87-1.93 (m, 2H), 1.57 (d, 3H, J=4 Hz).

Workup

  1. extractionextracted with DCM (3×25 mL)
  2. dry with materialThe combined organic extracts were dried with magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure to a golden oil
  5. customThe oil was purified
  6. washeluted with 50% ethyl acetate/hexanes
  7. extractionTarget band was extracted with ethyl acetate
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0dc5677eff204f6cada42ad9fb5619ba
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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