Hydrochloric Acid → HCID 90402706, compound

HRID 2200755Notes

Reaction equation

HRID 2200755 reaction equation
[Na].Br[C:3]1[N:11]([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:10]2[C:9](=[O:17])[N:8]([CH2:18][CH2:19][CH2:20][O:21][Si](C(C)(C)C)(C)C)[C:7](=[O:29])[N:6]([CH3:30])[C:5]=2[N:4]=1.Cl.[CH:32]([OH:35])([CH3:34])[CH3:33]>O>[OH:21][CH2:20][CH2:19][CH2:18][N:8]1[C:9](=[O:17])[C:10]2[N:11]([CH2:12][CH2:13][CH:14]([CH3:15])[CH3:16])[C:3]([O:35][CH:32]([CH3:34])[CH3:33])=[N:4][C:5]=2[N:6]([CH3:30])[C:7]1=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 5360545SodiumHCID 90402984HCID 90402984, compound2×

Product 1

HCID 90402706HCID 90402706, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium (0.12 g, 5.15 mmol) was dissolved in isopropanol (8 mL) and 8-bromo-1-(3-((tert-butyldimethylsilyl)oxy)propyl-7-isopentyl-3-methyl-1H-purine-2,6(3H,7H)-dione (0.50 g, 1.03 mmol, intermediate 82) was added. The reaction was stirred at room temperature for 15 h. The reaction was treated with 6N HCl to achieve pH=1, and stirred at room temperature for 1 h. The reaction was diluted with water (100 mL) and extracted with DCM (3×75 mL). The combined extracts were dried with magnesium sulfate, filtered and evaporated under reduced pressure to leave a golden oil. The oil was purified using two 2000 micron preparative TLC plate eluted with 50% ethyl acetate/hexanes to give 1-(3-hydroxypropyl)-7-isopentyl-8-isopropoxy-3-methyl-1H-purine-2,6(3H,7H)-dione (0.27 g, 75 yield) as a white solid. LCMS retention time=3.325 min and 97% purity, LCMS MH+=353. 1H NMR (CDCl3) δ 5.20-5.30 (m, 1H), 4.17 (t, 2H, J=8 Hz), 4.07 (t, 2H, J=8 Hz), 3.73 (t, 1H, J=8 Hz), 3.45-3.54 (m, 5H), 1.85-1.93 (m, 2H), 1.58-1.66 (m, 2H), 1.48-1.57 (m, 1H), 1.42 (d, 6H, J=8 Hz), 0.94 (d, 6H, J=8 Hz).

Workup

  1. stirringstirred at room temperature for 1 h
  2. extractionextracted with DCM (3×75 mL)
  3. dry with materialThe combined extracts were dried with magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto leave a golden oil
  7. customThe oil was purified
  8. washeluted with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-2b220fa72ddb42389ff415a58fcf72f2
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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