Benzyl Alcohol → 7-Benzyloxy-2,3-dimethylpyrrolo[2,3-d]pyridazine

HRID 1107816Notes

Reaction equation

HRID 1107816 reaction equation
Cl[C:2]1[N:3]=[N:4][CH:5]=[C:6]2[C:10]([CH3:11])=[C:9]([CH3:12])[NH:8][C:7]=12.[Na].[CH2:14]([OH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([O:21][C:2]1[N:3]=[N:4][CH:5]=[C:6]2[C:10]([CH3:11])=[C:9]([CH3:12])[NH:8][C:7]=12)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 244Benzyl Alcohol2×HCID 5360545SodiumHCID 18785595HCID 18785595, compound

Product 1

HCID 187856837-Benzyloxy-2,3-dimethylpyrrolo[2,3-d]pyridazine

Procedure

1.35 g (0.0074 mole) of 7-chloro-2,3-dimethylpyrrolo[2,3-d]pyridazine was added to a solution, obtained by adding 0.26 g (0.011 mole) of sodium to 25 ml of benzyl alcohol at room temperature, and the resulting mixture was heated at 115° C. and, in the course of the heating, 10 ml of benzyl alcohol were additionally added thereto. The heating was continued for 30 hours with stirring. After completion of the reaction, the reaction mixture was poured into ice-water and extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure and benzyl alcohol was distilled off under reduced pressure. The residue was purified by column chromatography through silica gel using a 20:1 mixture of chloroform and methanol as an eluent to give 1.15 g of 7-benzyloxy-2,3-dimethylpyrrolo[2,3-d]pyridazine as a pale yellow powder.

Workup

  1. customobtained
  2. additionwere additionally added
  3. customAfter completion of the reaction
  4. extractionextracted with dichloromethane
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure and benzyl alcohol
  7. distillationwas distilled off under reduced pressure
  8. customThe residue was purified by column chromatography through silica gel using
  9. additiona 20:1 mixture of chloroform and methanol as an eluent

Sources & evidence

ORD record
ord-71f6d28a470c49d49dcff88d79c29b53
Source dataset
uspto-grants-2000_05
Patent number
US06063782

Reaction notes

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