Hydrochloric Acid → HCID 90402936, compound

HRID 2200742Notes

Reaction equation

HRID 2200742 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]([O:30][CH:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[N:16][C:15]=2[N:14]([CH3:36])[C:13]1=[O:37])(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:37])[N:14]([CH3:36])[C:15]=3[N:16]=[C:17]2[O:30][CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 904026851-(3-((tert-butyldimethylsilyl)oxy)propyl)-7-(4-chlorobenzyl)-8-(cyclopentyloxy)-3-methyl-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 90402936HCID 90402936, compoundYield 14.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Step 2 1-(3-((tert-Butyldimethylsilyl)oxy)propyl)-7-(4-chlorobenzyl)-8-(cyclopentyloxy)-3-methyl-1H-purine-2,6(3H,7H)-dione (0.25 g, 0.46 mmol) was dissolved in ethanol (5 mL) and 6N aqueous HCl (1 mL) was added. The clear solution was stirred at room temperature for 1 h. The reaction was diluted with water (100 mL) and extracted with ethyl acetate (3×100 mL). The combined extracts were dried with magnesium sulfate, filtered and the solvent was removed under reduced pressure to a golden oil. The oil was purified using a 2000 micron preparative TLC plate eluted with ethyl acetate. Target band was scraped off plate, eluted off silica gel with ethyl acetate and evaporated under reduced pressure to give 7-(4-chlorobenzyl)-8-(cyclopentyloxy)-1-(3-hydroxypropyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (0.028 g, 14% yield) as a white solid. LCMS retention time=3.656 min and 98% purity, LCMS MH+ 433. 1H NMR (DMSO-d6) δ 7.34 (dd, 4H, J=12 and 48 Hz), 5.34-5.40 (m, 1H), 5.18 (s, 2H), 4.42 (t, 1H, J=4 Hz), 3.89 (t, 2H, J=8 Hz), 3.38-3.45 (m, 2H), 3.36 (s, 3H), 1.55-1.93 (m, 8H).

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. dry with materialThe combined extracts were dried with magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure to a golden oil
  5. customThe oil was purified
  6. washeluted with ethyl acetate
  7. washeluted off silica gel with ethyl acetate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9003758d03a244b9aa17f0d32c3b2616
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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