Carbon Dioxide → HCID 135738540, compound

HRID 1532065Notes

Reaction equation

HRID 1532065 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[CH:9][C:10]([O:26][CH2:27][CH3:28])=[C:11]([C:13]2[NH:14][C:15](=[O:25])[C:16]3[CH:21]=[N:20][N:19]([CH2:22][CH2:23][CH3:24])[C:17]=3[N:18]=2)[CH:12]=1.[C:29](=[O:31])=[O:30].[Cl-].[NH4+]>C1COCC1>[CH2:27]([O:26][C:10]1[CH:9]=[CH:8][C:7]([C:29]([OH:31])=[O:30])=[CH:12][C:11]=1[C:13]1[NH:14][C:15](=[O:25])[C:16]2[CH:21]=[N:20][N:19]([CH2:22][CH2:23][CH3:24])[C:17]=2[N:18]=1)[CH3:28]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 25517Ammonium ChlorideHCID 135738546HCID 135738546, compoundHCID 178418339Butyllithium

Product 1

HCID 135738540HCID 135738540, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (2.5 M solution in hexane, 2.0 ml, 0.005 mol) was added dropwise to a stirred solution of 6-(5-bromo-2-ethoxyphenyl)-1-n-propyl-1,5-dihydro-4H-pyrazolo[3, 4-d]pyrimidin-4-one (0.755 g, 0.002 mol) in dry THF (20 ml) at −78° C. under a dry nitrogen atmosphere. The bright yellow solution was stirred for 1 hour at −78° C., then excess crushed solid carbon dioxide was added and the resulting solution was allowed to warm to room temperature. Saturated aqueous ammonium chloride solution (3 ml) was then added and the solvents removed by evaporation under vacuum. The residue was partitioned between saturated aqueous sodium carbonate solution (30 ml) and dichloromethane (30 ml), the organic phase was removed and the aqueous phase extracted with further dichloromethane (3×30 ml). The aqueous phase was then acidified to pH 1 with concentrated hydrochloric acid and extracted with ethyl acetate (5×40 ml). The combined ethyl acetate extracts were dried (Na2SO4) and the solvent removed by evaporation under vacuum to give a white solid. Crystallisation from ethyl acetate-methanol gave the title compound as a white powder (0.130 g, 19%), m.p. 277-279° C. Found: C,59.64; H,5.19; N,16.39. C17H18N4O4 requires C,59.64; H,5.23; N,16.37%.

Workup

  1. additionwas added
  2. temperatureto warm to room temperature
  3. customthe solvents removed by evaporation under vacuum
  4. customThe residue was partitioned between saturated aqueous sodium carbonate solution (30 ml) and dichloromethane (30 ml)
  5. customthe organic phase was removed
  6. extractionthe aqueous phase extracted with further dichloromethane (3×30 ml)
  7. extractionextracted with ethyl acetate (5×40 ml)
  8. dry with materialThe combined ethyl acetate extracts were dried (Na2SO4)
  9. customthe solvent removed by evaporation under vacuum
  10. customto give a white solid
  11. customCrystallisation from ethyl acetate-methanol

Sources & evidence

ORD record
ord-0c10a0cc12d147019c6f83f17fd8cb87
Source dataset
uspto-grants-2001_03
Patent number
US06200980B1

Reaction notes

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