Water → 1-Benzyl-7-(4-fluorobenzyloxy)-3-hydroxymethyl-2-methylpyrrolo[2,3-d]pyridazine

HRID 1734516Notes

Reaction equation

HRID 1734516 reaction equation
[CH2:1]([N:8]1[C:12]2=[C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[N:14]=[N:15][CH:16]=[C:11]2[C:10]([CH:26]=[O:27])=[C:9]1[CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>C(O)C>[CH2:1]([N:8]1[C:12]2=[C:13]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=3)[N:14]=[N:15][CH:16]=[C:11]2[C:10]([CH2:26][OH:27])=[C:9]1[CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 19437750HCID 19437750, compound

Product 1

HCID 99516271-Benzyl-7-(4-fluorobenzyloxy)-3-hydroxymethyl-2-methylpyrrolo[2,3-d]pyridazineYield 85.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 780 mg (2.08 mmol) of 1-benzyl-7-(4-fluorobenzyloxy) 3-formyl-2 -methylpyrrolo [2,3-d]pyridazine in 50 ml of ethanol is treated with 80 mg (2.1 mmol) of sodium borohydride and stirred at room temperature for 30 min. After addition of 100 ml of water, the mixture is concentrated on a rotary evaporator to half the volume. The precipitate is filtered off, washed with 50 ml of water and dried in a high vacuum over potassium hydroxide. 670 mg (85%) of the title compound are isolated. M.p.: 122°-124° C.

Workup

  1. concentrationthe mixture is concentrated on a rotary evaporator to half the volume
  2. filtrationThe precipitate is filtered off
  3. washwashed with 50 ml of water
  4. dry with materialdried in a high vacuum over potassium hydroxide

Sources & evidence

ORD record
ord-3ffe58a2c7514000ac12b594c3066a17
Source dataset
uspto-grants-1996_07
Patent number
US05534515

Reaction notes

Loading…