Sodium Bicarbonate → HCID 9933486, compound

HRID 377612Notes

Reaction equation

HRID 377612 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH3:9][N:10]1[C:15](=[O:16])[C:14]2=[CH:17][N:18]([CH2:20][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)[N:19]=[C:13]2[N:12]([CH2:31][C:32]([CH3:34])=[CH2:33])[C:11]1=[O:35].CC1C=C[C:40]([S:43](OCCCO[Si](C)(C)C(C)(C)C)(=O)=S)=[CH:39]C=1.[C:58](=[O:61])(O)[O-].[Na+]>O1CCCC1>[OH:61][CH2:58][CH2:39][CH2:40][S:43][C:17]1[N:18]([CH2:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23][CH:22]=2)[N:19]=[C:13]2[C:14]=1[C:15](=[O:16])[N:10]([CH3:9])[C:11](=[O:35])[N:12]2[CH2:31][C:32]([CH3:34])=[CH2:33]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 2724682Lithium diisopropylamideHCID 19356087HCID 19356087, compoundHCID 53747051HCID 53747051, compound

Product 1

HCID 9933486HCID 9933486, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

A solution of lithium diisopropylamide (1.12 mmol) in tetrahydrofuran (6 ml) was added dropwise to a stirred solution of 5-methyl-7-(2-methyl-2-propenyl)-2-(1-naphthalenylmethyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6[5H,7H]-dione (0.20 g) and 3-{[dimethyl(1,1-dimethylethyl)silyl]oxy }propyl 4-methylphenylthiosulfonate (J. Med. Chem. 1995, 38, 2557) (0.262 g) in anhydrous tetrahydrofuran (20 ml) at -70° C. The solution was stirred for a further 1 hour at -70° C. and then allowed to warm to room temperature. Saturated aqueous sodium bicarbonate solution (10 ml) was added and the mixture was extracted with ethyl acetate. The organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residual oil was purified by column chromatography over silica eluting with acetone:hexane (1:5). The product was dissolved in acetonitrile (5 ml) and treated with 40% aqueous hydrofluoric acid (1 ml). After 5 minutes, the solution was neutralised with aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic extracts were washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica eluting with acetone:hexane (1:5 then 1:3) followed by recrystallisation from diethyl ether/hexane to give the title compound (0.11 g).

Workup

  1. temperatureto warm to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residual oil was purified by column chromatography over silica eluting with acetone:hexane (1:5)
  7. dissolutionThe product was dissolved in acetonitrile (5 ml)
  8. additiontreated with 40% aqueous hydrofluoric acid (1 ml)
  9. waitAfter 5 minutes
  10. extractionextracted with ethyl acetate
  11. washThe organic extracts were washed with saturated aqueous sodium bicarbonate solution
  12. dry with materialdried over anhydrous magnesium sulfate
  13. filtrationfiltered
  14. customevaporated under reduced pressure
  15. customThe residue was purified by column chromatography over silica eluting with acetone:hexane (1:5
  16. custom1:3) followed by recrystallisation from diethyl ether/hexane

Sources & evidence

ORD record
ord-293ce576df804211976be6de34d4f7f1
Source dataset
uspto-grants-2000_02
Patent number
US06028074

Reaction notes

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