Sodium borohydride → HCID 57597336, compound

HRID 1926048Notes

Reaction equation

HRID 1926048 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:19]3[C:20](=[CH:24][N:25]([C:27]4[CH:34]=[CH:33][C:30]([CH:31]=[O:32])=[CH:29][CH:28]=4)[N:26]=3)[N:21]=[CH:22][N:23]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:19]3[C:20](=[CH:24][N:25]([C:27]4[CH:28]=[CH:29][C:30]([CH2:31][OH:32])=[CH:33][CH:34]=4)[N:26]=3)[N:21]=[CH:22][N:23]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86615765HCID 86615765, compound

Product 1

HCID 57597336HCID 57597336, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[7-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-2H-pyrazolo[4,3-d]pyrimidin-2-yl]benzaldehyde (50 mg) in methanol (2 mL) was added sodium borohydride (2 mg) under ice-cooling, and the mixture was stirred for 30 min. After the completion of the reaction, the reaction solution was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (tetrahydrofuran/ethyl acetate=1/1) to give the title compound (20 mg) as a white solid.

Workup

  1. temperaturecooling
  2. customAfter the completion of the reaction
  3. concentrationthe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ee02d908b6834e04bec4b46503111e24
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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