Tetrahydrofuran → HCID 66602658, compound

HRID 2097506Notes

Reaction equation

HRID 2097506 reaction equation
[O:1]1CCC[CH2:2]1.[Br:6][C:7]1[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:10]2[CH:11]=[N:12][N:13]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:14](=[O:15])[C:9]=2[C:8]=1[CH2:33]Br.CO.C[O-].[Na+]>O>[Br:6][C:7]1[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:30])[CH3:31])[C:10]2[CH:11]=[N:12][N:13]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:14](=[O:15])[C:9]=2[C:8]=1[CH2:33][O:1][CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23694274Sodium methanolate methanolHCID 66602679HCID 66602679, compound

Product 1

HCID 66602658HCID 66602658, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 4 ml of tetrahydrofuran solution containing 459 mg (0.81 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 4 ml of 28% sodium methoxide methanol solution, and the mixture was stirred at room temperature 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 after separation was washed successively with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=4:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 359 mg of the title compound as a colorless oil. (Yield: 86%)

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe organic layer after separation
  4. washwas washed successively with water
  5. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionthe fractions containing the desired compound
  8. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-13eaff92a28b4ac5ba1ab2c37a1460ea
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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