Hydrochloric Acid → 4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carbaldehyde

HRID 480164Notes

Reaction equation

HRID 480164 reaction equation
[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[N:8]=[C:7]([C:14]34[CH2:21][C:18]([C:22](O)=[O:23])([CH2:19][CH2:20]3)[CH2:17][CH2:16][CH2:15]4)[NH:6][C:5]=2[C:4](=[O:25])[N:3]1[CH2:26][CH2:27][CH3:28].C(N(CC)CC)C.C(OCC)(=O)C.Cl>CS(C)=O>[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[N:8]=[C:7]([C:14]34[CH2:15][CH2:16][C:18]([CH:22]=[O:23])([CH2:17][CH2:21]3)[CH2:19][CH2:20]4)[NH:6][C:5]=2[C:4](=[O:25])[N:3]1[CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 98432695-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[3.2.1]octane-1-carboxylic acid

Product 1

HCID 99294054-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carbaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

8-(4-Hydroxymethyl-bicyclo[2.2.2]oct-1-yl)-1,3-dipropyl-3,7-dihydropurine-2,6-dione (X, Example 8, 0.440 kg) and dimethyl sulphoxide (1.76 l) are mixed under nitrogen, stirred for 5 to 15 mins and triethylamine (1.065 l) is added. A mixture of sulphur trioxide pyridine complex (0.561 kg) in dimethyl sulphoxide (2.64 l) is added, maintaining the internal temperature below 30° C. The internal temperature is adjusted to 14 to 20° C. and the reaction mixture is stirred at 14 to 20° C. for 20 hours. Ethyl acetate (8.80 l) and hydrochloric acid (1 M, 4.40 l) are added to the reaction and the mixture is stirred vigorously for 15 mins. The layers are separated and the organic layer is washed twice more with hydrochloric acid (1 M, 4.40 l). The organic layer is then washed with saline (2.20 l), dried over magnesium sulfate (0.223 kg) for 10 mins, filtered and the filter cake is washed with ethyl acetate (0.440 l). The solvent is evaporated under reduced pressure at 40 to 45° to give the title compound.

Workup

  1. additionis added
  2. temperaturemaintaining the internal temperature below 30° C
  3. customis adjusted to 14 to 20° C.
  4. stirringthe reaction mixture is stirred at 14 to 20° C. for 20 hours
  5. stirringthe mixture is stirred vigorously for 15 mins
  6. customThe layers are separated
  7. washthe organic layer is washed twice more with hydrochloric acid (1 M, 4.40 l)
  8. washThe organic layer is then washed with saline (2.20 l)
  9. dry with materialdried over magnesium sulfate (0.223 kg) for 10 mins
  10. filtrationfiltered
  11. washthe filter cake is washed with ethyl acetate (0.440 l)
  12. customThe solvent is evaporated under reduced pressure at 40 to 45°

Sources & evidence

ORD record
ord-39d0ab0abe5448ae821467d8ea52af63
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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