HCID 18173123, compound → HCID 18173107, compound

HRID 395868Notes

Reaction equation

HRID 395868 reaction equation
[Li][CH2:2][CH2:3][CH2:4][CH3:5].O=C1[CH:12]2[CH:10]3[CH:11]2CC1[CH:9]3[C:14]1[NH:22][C:21]2[C:20](=[O:23])[N:19]([CH2:24][CH2:25][CH3:26])[C:18](=[O:27])[N:17]([CH2:28][CH2:29][CH3:30])[C:16]=2[N:15]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:5]=[C:4]1[CH:11]2[CH:10]3[CH:12]2[CH2:2][CH:3]1[CH:9]3[C:14]1[NH:22][C:21]2[C:20](=[O:23])[N:19]([CH2:24][CH2:25][CH3:26])[C:18](=[O:27])[N:17]([CH2:28][CH2:29][CH3:30])[C:16]=2[N:15]=1

Participants

5

Reactant 2

HCID 18173123HCID 18173123, compoundHCID 178418339Butyllithium

Product 1

HCID 18173107HCID 18173107, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl-triphenyl-phosphonium bromide (2.08 g) was taken in THF (50 ml) at −78° C. nBuLi (3.66 ml, 1.6 M) was added slowly at −78° C. and stirred for 1 hr. 8-(5-Oxo-tricyclo[2.2.1.02,6]hept-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (Example 1) (1 g) was dissolved in THF and added to the reaction mixture at −78° C. slowly. After the addition was over, the reaction mixture was allowed to warmed to room temperature slowly and stirred at room temperature overnight. The next day, the reaction mixture was quenched with 1N HCl and extracted with ethyl acetate (3×50 ml). The combined organic layer was washed with water, brine and dried over Na2SO4. After concentration the product was purified by silica gel column. Mass (ES+ 341).

Workup

  1. additionwas added slowly at −78° C.
  2. additionadded to the reaction mixture at −78° C. slowly
  3. additionAfter the addition
  4. stirringstirred at room temperature overnight
  5. customThe next day, the reaction mixture was quenched with 1N HCl
  6. extractionextracted with ethyl acetate (3×50 ml)
  7. washThe combined organic layer was washed with water, brine
  8. dry with materialdried over Na2SO4
  9. concentrationAfter concentration the product
  10. customwas purified by silica gel column

Sources & evidence

ORD record
ord-39217ac792cd4e2a85e58a7eaff5a94e
Source dataset
uspto-grants-2003_08
Patent number
US06605600B1

Reaction notes

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