Triethylamine → 4-(2,6-Dioxo-3-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carbaldehyde

HRID 395281Notes

Reaction equation

HRID 395281 reaction equation
[OH:1][CH2:2][C:3]12[CH2:10][CH2:9][C:6]([C:11]3[NH:19][C:18]4[C:17](=[O:20])[NH:16][C:15](=[O:21])[N:14]([CH2:22][CH2:23][CH3:24])[C:13]=4[N:12]=3)([CH2:7][CH2:8]1)[CH2:5][CH2:4]2.CCN(CC)CC>CS(C)=O.CCOC(C)=O>[O:21]=[C:15]1[N:14]([CH2:22][CH2:23][CH3:24])[C:13]2[N:12]=[C:11]([C:6]34[CH2:7][CH2:8][C:3]([CH:2]=[O:1])([CH2:10][CH2:9]3)[CH2:4][CH2:5]4)[NH:19][C:18]=2[C:17](=[O:20])[NH:16]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 11994549HCID 11994549, compound

Product 1

HCID 119942814-(2,6-Dioxo-3-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carbaldehydeYield 33.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

8-(4-Hydroxymethyl-bicyclo[2.2.2]oct-1-yl)-3-propyl-3,7-dihydro-purine-2,6-dione (2.70 g, 8.13 mmol) was dissolved in 40 mL of DMSO. Pyridine-SO3 (3.88 g, 3 eq) was added, followed by Et3N (7.4 mL, 7 eq) at rt. The resulting reaction mixture was stirred at rt for 18 h. It was then diluted with EtOAc and washed with 5% aq citric acid, H2O, brine, dried (Na2SO4) and concentrated under reduced pressure to afford 900 mg of the desired aldehyde.

Workup

  1. customThe resulting reaction mixture
  2. washwashed with 5% aq citric acid, H2O, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3b56c0a39707463fabdc42a694013200
Source dataset
uspto-grants-2003_08
Patent number
US06605601B2

Reaction notes

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