Hydrochloric Acid → HCID 90403185, compound

HRID 2200754Notes

Reaction equation

HRID 2200754 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][CH2:23][CH:24]([CH3:26])[CH3:25])[C:17]([O:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=3)=[N:16][C:15]=2[N:14]([CH3:35])[C:13]1=[O:36])(C(C)(C)C)(C)C.Cl>C(O)C.O>[Cl:34][C:30]1[CH:29]=[C:28]([CH:33]=[CH:32][CH:31]=1)[O:27][C:17]1[N:18]([CH2:22][CH2:23][CH:24]([CH3:25])[CH3:26])[C:19]2[C:20](=[O:21])[N:12]([CH2:11][CH2:10][CH2:9][OH:8])[C:13](=[O:36])[N:14]([CH3:35])[C:15]=2[N:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131735713HCID 131735713, compound

Product 1

HCID 90403185HCID 90403185, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Step 2 1-(3-((tert-Butyldimethylsilyl)oxy)propyl-8-(3-chlorophenoxy)-7-isopentyl-3-methyl-1H-purine-2,6(3H,7H)-dione (0.55 g, 1.03 mmol) was dissolved in ethanol (10 mL) and 6N HCl (2 mL) was added and the reaction was stirred at room temperature for 1 h. The reaction was diluted with water (100 mL) and extracted with DCM (3×75 mL). The combined extracted were dried with magnesium sulfate, filtered and evaporated under reduced pressure to leave a golden oil. The oil was purified using a 24 g silica gel flash column eluted with 50% ethyl acetate/hexanes to give 8-(3-chlorophenoxy)-1-(3-hydroxypropyl)-7-isopentyl-3-methyl-1H-purine-2,6(3H,7H)-dione (0.21 g, 49% yield) as a white solid. LCMS retention time=3.859 min and 98% purity, LCMS MH+=421. 1H NMR (CDCl3) δ 7.35-7.38 (m, 2H), 7.24-7.28 (m, 1H), 7.18-7.25 (m, 1H), 4.27 (t, 2H, J=8 Hz), 4.20 (t, 2H, J=8 Hz), 3.52-3.58 (m, 3H), 3.47 (s, 3H), 1.86-1.94 (m, 2H), 1.70-1.78 (m, 2H), 1.59-1.69 (m, 1H), 0.98 (d, 6H, J=8 Hz).

Workup

  1. extractionextracted with DCM (3×75 mL)
  2. extractionThe combined extracted
  3. dry with materialwere 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-df8e47b6b8a94ea596d696639afe58f8
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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