Water → HCID 69059040, compound

HRID 2105660Notes

Reaction equation

HRID 2105660 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[CH2:22][C:18](C=O)([CH2:19][CH2:20][CH2:21]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[O:30][C:31](=[O:33])[CH3:32].[Li+].[OH-].O.[CH2:37]1COCC1>CO>[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[N:8]=[C:7]([C:14]34[CH2:22][CH:18]([CH2:19][CH2:20][CH2:21]3)[CH2:17][CH2:16][CH:15]4[CH:37]=[CH:32][C:31]([OH:30])=[O:33])[NH:6][C:5]=2[C:4](=[O:25])[N:3]1[CH2:26][CH2:27][CH3:28]

Participants

7

Reactant 5

HCID 962WaterHCID 3939Lithium HydroxideHCID 6584Methyl Acetate2×HCID 8028TetrahydrofuranHCID 18767627HCID 18767627, compound

Product 1

HCID 69059040HCID 69059040, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[3.3.1]nonane-1-carbaldehyde (355 mg) was taken in THF (25 ml): Triphenyl-□□-phosphanylidene)-acetic acid methyl ester (614 mg) was added and refluxed overnight. Next day another 460 mg of Triphenyl-□□-phosphanylidene)-acetic acid methyl ester was added and refluxed for 24 hrs. Cooled to RT LiOH (210 mg), water (2 ml), MeOH (5 ml) were added and stirred at rt overnight. Solvent was removed under reduced pressure. Diluted with water (25 ml), extracted with ethyl acetate (3×25 ml). Aqueous layer was acidified with 1 N HCl and extracted with ethyl acetate (3×50 ml), dried over Na2SO4 and concentrated. Yield 254 mg.

Workup

  1. temperaturerefluxed overnight
  2. temperaturerefluxed for 24 hrs
  3. additionwere added
  4. customSolvent was removed under reduced pressure
  5. additionDiluted with water (25 ml)
  6. extractionextracted with ethyl acetate (3×25 ml)
  7. extractionextracted with ethyl acetate (3×50 ml)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-469a28ac369a49479184baedfaa577c6
Source dataset
uspto-grants-2009_08
Patent number
US07579354B2

Reaction notes

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