Tetrahydrofuran → HCID 66602418, compound

HRID 2097543Notes

Reaction equation

HRID 2097543 reaction equation
O1CCCC1.[CH3:6][CH2:7][CH:8]([OH:11])[CH2:9][CH3:10].[H-].[Na+].[Br:14][C:15]1[N:32]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:18]2[CH:19]=[N:20][N:21]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:22](=[O:23])[C:17]=2[C:16]=1[CH2:41]Br>O>[Br:14][C:15]1[N:32]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:18]2[CH:19]=[N:20][N:21]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:22](=[O:23])[C:17]=2[C:16]=1[CH2:41][O:11][CH:8]([CH2:9][CH3:10])[CH2:7][CH3:6]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 114283-PentanolHCID 24758Sodium hydrideHCID 66602679HCID 66602679, compound

Product 1

HCID 66602418HCID 66602418, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 15 ml of dehydrated tetrahydrofuran solution containing 1.90 ml of 3-pentanol was added 0.38 g of sodium hydride (55% dispersed material in mineral oil) under cooling in ice-bath, and the mixture was stirred at room temperature for 3 hours. Then, 0.99 g (1.75 mmol) of 2-bromo-3-bromomethyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Reference example 25-(a) was added to the mixture, and the mixture was stirred at 45° C. for 2 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then, concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=7:3 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 0.66 g of the title compound as a slightly yellowish oil. (Yield: 65%)

Workup

  1. temperatureunder cooling in ice-bath
  2. addition25-(a) was added to the mixture
  3. stirringthe mixture was stirred at 45° C. for 2 hours
  4. additionwas added to the reaction mixture
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionthe fractions containing the desired compound
  10. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-4d28db0a66d14d8ba4961d396c84484c
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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