Triethylamine → HCID 59574259, compound

HRID 2092028Notes

Reaction equation

HRID 2092028 reaction equation
Br[C:2]1[C:3]([CH:8]([N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH2:9][CH3:10])=[N:4][CH:5]=[N:6][CH:7]=1.C(N(CC)CC)C.[H][H]>CO.[C].[Pd]>[N:6]1[CH:7]=[CH:2][C:3]([CH:8]([N:11]2[C:12](=[O:21])[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:19]2=[O:20])[CH2:9][CH3:10])=[N:4][CH:5]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 59574581HCID 59574581, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59574259HCID 59574259, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2-[1-(5-Bromopyrimidin-4-yl)propyl]isoindoline-1,3-dione (568 mg, 1.64 mmol), triethylamine (0.228 mL, 1.64 mmol) and 10% palladium-carbon (50 wt %, 100 mg) were stirred in methanol (10 mL) in a hydrogen atmosphere at room temperature for 1 day. The reaction solution was filtered through celite and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) give the desired product (292 mg, 66% yield).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. customevaporated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-a9cc426c049c4a09a35f9673a8004af1
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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