Water → HCID 57597232, compound

HRID 1926065Notes

Reaction equation

HRID 1926065 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([NH:18][C:19]2[C:20]3[N:27]([CH2:28][CH2:29][O:30][CH2:31][CH2:32][OH:33])[CH:26]=[CH:25][C:21]=3[N:22]=[CH:23][N:24]=2)[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([C:11](=[O:13])[CH3:12])[CH:8]=[CH:9][CH:10]=1.[BH4-].[Na+].O>CO>[Cl:1][C:2]1[CH:17]=[C:16]([NH:18][C:19]2[C:20]3[N:27]([CH2:28][CH2:29][O:30][CH2:31][CH2:32][OH:33])[CH:26]=[CH:25][C:21]=3[N:22]=[CH:23][N:24]=2)[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:11]([OH:13])[CH3:12])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 57597191HCID 57597191, compound

Product 1

HCID 57597232HCID 57597232, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-{3-[2-chloro-4-({5-[2-(2-hydroxyethoxy)ethyl]-5H-pyrrolo[3,2-d]pyrimidin-4-yl}amino)phenoxy]phenyl}ethanone (233 mg) in methanol (5 mL) was added sodium borohydride (38 mg), and the mixture was stirred at room temperature for 2 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was crystallized from ethyl acetate-diethyl ether to give the title compound (225 mg) as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was crystallized from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-ec51911483904750a5974d11a160f995
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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