Water → HCID 67079115, compound

HRID 480130Notes

Reaction equation

HRID 480130 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]([CH:23]=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>C1COCC1.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][C:18]([CH:23]=[CH:32][C:31]([OH:33])=[O:30])([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]

Participants

7

Reactant 4

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

Product 1

HCID 67079115HCID 67079115, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

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. Mass (ES+ 429).

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-d49abf32c58c42f1b0e8aa8ea20d2be0
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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