Dimethylformamide → HCID 66602606, compound

HRID 2097542Notes

Reaction equation

HRID 2097542 reaction equation
CN(C)C=O.[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.[CH3:35][C:36]([CH3:39])([O-:38])[CH3:37].[Na+]>O>[Br:6][C:7]1[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:31])([CH3:30])[CH3:32])[C:10]2[CH:11]=[N:12][N:13]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:22])([CH3:23])[CH3:21])[C:14](=[O:15])[C:9]=2[C:8]=1[CH2:33][O:38][C:36]([CH3:39])([CH3:37])[CH3:35]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 23676156Sodium t-butoxideHCID 66602679HCID 66602679, compound

Product 1

HCID 66602606HCID 66602606, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 50 ml of N,N-dimethylformamide solution containing 2.52 g (4.44 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 0.43 g (4.44 mmol) of sodium tert-butoxide at −10° C., and the mixture was stirred at the same temperature for 3 hours. The mixture was further stirred at 0° C. for 10 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with toluene. The organic layer after separation was washed successively with water and then 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=98:2→65:35 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 0.61 g of the title compound as a pale yellowish solid. (Yield: 25%)

Workup

  1. stirringThe mixture was further stirred at 0° C. for 10 hours
  2. additionwas added to the reaction mixture
  3. extractionthe mixture was extracted with toluene
  4. customThe organic layer after separation
  5. washwas washed successively with water
  6. dry with materialwith a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionthe fractions containing the desired compound
  9. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-398954994da2493c840c3f90e736d8ff
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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