Hydrochloric Acid → HCID 90403084, compound

HRID 2200748Notes

Reaction equation

HRID 2200748 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:34])[CH:31]([CH3:33])[CH3:32])=[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.C(OCC)C>[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:36])[N:14]([CH3:35])[C:15]=3[N:16]=[C:17]2[CH:30]([OH:34])[CH:31]([CH3:32])[CH3:33])=[CH:28][CH:27]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 904029981-(3-((tert-butyldimethylsilyl)oxy)propyl)-7-(4-chlorobenzyl)-8-(1-hydroxy-2-methylpropyl)-3-methyl-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 90403084HCID 90403084, compoundYield 56.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Step 2 1-(3-((tert-Butyldimethylsilyl)oxy)propyl)-7-(4-chlorobenzyl)-8-(1-hydroxy-2-methylpropyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (0.19 g, 0.355 mmol) was dissolved in ethanol (5 mL) and 6 N HCl (0.5 mL) was added. The clear solution was stirred at room temperature for 1 h. The reaction was diluted with water (75 mL) and extracted with DCM (3×50 ml). The combined extracts were dried with magnesium sulfate, filtered and the solvent was removed under reduced pressure to yield a white solid. Solid was slurried in diethyl ether (4 mL) and collected to give 7-(4-chlorobenzyl)-8-(1-hydroxy-2-methylpropyl)-1-(3-hydroxypropyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (0.085 g, 56% yield) as a white solid. LCMS retention time=3.263 min and 94% purity, LCMS MH+ 421. 1H NMR (CDCl3) δ 7.23 (dd, 4H, J=8 Hz and 68 Hz), 5.59 (dd, 2H, J=16 Hz and 40 Hz), 4.43 (t, 1H, J=8 Hz). 4.17 (t, 2H, J=8 Hz), 3.59 (s, 3H), 3.48-3.54 (m, 2H), 3.35-3.40 (m, 1H), 2.48 (d, 1H, J=8 Hz), 2.08-2.16 (m, 1H), 1.85-1.92 (m, 2H), 1.03 (d, 3H, J=8 Hz), 0.82 (d, 3H, J=8 Hz).

Workup

  1. extractionextracted with DCM (3×50 ml)
  2. dry with materialThe combined extracts were dried with magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customto yield a white solid
  6. customcollected

Sources & evidence

ORD record
ord-69f91296dd1547dea32d82512059a16c
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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