HCID 10109179, compound → HCID 9946871, compound

HRID 395875Notes

Reaction equation

HRID 395875 reaction equation
[OH:1][CH:2]1[CH:8]2[CH2:9][CH:5]([CH2:6][CH:7]2[C:10]2[NH:18][C:17]3[C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH3:22])[C:14](=[O:23])[N:13]([CH2:24][CH2:25][CH3:26])[C:12]=3[N:11]=2)[CH2:4][CH2:3]1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl.CCOCC>[O:1]=[C:2]1[CH:8]2[CH2:9][CH:5]([CH2:6][CH:7]2[C:10]2[NH:18][C:17]3[C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH3:22])[C:14](=[O:23])[N:13]([CH2:24][CH2:25][CH3:26])[C:12]=3[N:11]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 10109179HCID 10109179, compoundHCID 178418287HCID 178418287, compound2×

Product 1

HCID 9946871HCID 9946871, compoundYield 46.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

8-(4-Hydroxy-bicyclo[3.2.1]oct-6-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (140 mg) from step 1 was taken in CH2Cl2 (5 ml). Celite (2 g) was added, followed by PCC (90 mg) and stirred at room temperature for 1 hr. Additional PCC (90 mg) was added and stirred for 2 hrs at room temperature. The reaction mixture was diluted with ether (100 ml) and filtered through celite and concentrated. Purified on silica column eluted with ethyl acetate:hexane (25:75) to yield 65 mg of the desired product. Mass (ES+ 369).

Workup

  1. additionCelite (2 g) was added
  2. stirringstirred for 2 hrs at room temperature
  3. filtrationfiltered through celite and
  4. concentrationconcentrated
  5. customPurified on silica column
  6. washeluted with ethyl acetate:hexane (25:75)

Sources & evidence

ORD record
ord-dd0c7c0ee1694c6896555f6b33522ac2
Source dataset
uspto-grants-2003_08
Patent number
US06605600B1

Reaction notes

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