Methoxymethyl-triphenylphosphonium chloride → HCID 69267631, compound

HRID 395869Notes

Reaction equation

HRID 395869 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].O=[C:35]1[CH:40]2[CH:38]3[CH:39]2[CH2:41][CH:36]1[CH:37]3[C:42]1[NH:50][C:49]2[C:48](=[O:51])[N:47]([CH2:52][CH2:53][CH3:54])[C:46](=[O:55])[N:45]([CH2:56][CH2:57][CH3:58])[C:44]=2[N:43]=1>C1(C)C=CC=CC=1>[CH3:2][O:3][CH:4]=[C:35]1[CH:40]2[CH:38]3[CH:39]2[CH2:41][CH:36]1[CH:37]3[C:42]1[NH:50][C:49]2[C:48](=[O:51])[N:47]([CH2:52][CH2:53][CH3:54])[C:46](=[O:55])[N:45]([CH2:56][CH2:57][CH3:58])[C:44]=2[N:43]=1

Participants

5

Reactant 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 18173123HCID 18173123, compound

Product 1

HCID 69267631HCID 69267631, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Methoxymethyl-triphenyl-phosphonium chloride (1.1 g) was taken in toluene (10 ml) at 0° C. Potassium bis(trimethylsilyl)amide (0.5 M in toluene, 12.8 ml) was added and stirred at 0° C. 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 added to the reaction mixture, which was then warmed to room temperature and stirred overnight. The next day, the reaction mixture was quenched with water, and extracted with ethyl acetate (3×50 ml). The combined organic layer was washed with water and brine, and dried over Na2SO4. After concentration, the crude product (620 mg) was purified by column. Mass (ES+ 371).

Workup

  1. temperaturewas then warmed to room temperature
  2. stirringstirred overnight
  3. customThe next day, the reaction mixture was quenched with water
  4. extractionextracted with ethyl acetate (3×50 ml)
  5. washThe combined organic layer was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationAfter concentration
  8. customthe crude product (620 mg) was purified by column

Sources & evidence

ORD record
ord-8a00d05c60624efebeb91a1d2aa6893d
Source dataset
uspto-grants-2003_08
Patent number
US06605600B1

Reaction notes

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