Acetonitrile → HCID 22349452, compound

HRID 896015Notes

Reaction equation

HRID 896015 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:15][C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)[CH:12]=2)[C:7]1=[O:23])[CH3:2].Br[C:25]1([CH2:34][CH2:35][O:36][CH3:37])[C:30](=[O:31])[NH:29][C:28](=[O:32])[NH:27][C:26]1=[O:33].C1CN2C(=NCCC2)NC1.C(#N)C>CO.C(O)(=O)C>[CH:11]([O:15][CH:16]([CH3:21])[CH3:17])([CH3:12])[CH3:10].[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][C:25]4([CH2:34][CH2:35][O:36][CH3:37])[C:26](=[O:33])[NH:27][C:28](=[O:32])[NH:29][C:30]4=[O:31])=[CH:18][CH:17]=3)[CH:12]=2)[C:7]1=[O:23])[CH3:2]

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 79873TriazabicyclodeceneHCID 219311515-Bromo-5-(2-methoxyethyl)pyrimidine-2,4,6(1H,3H,5H)-trioneHCID 22349419HCID 22349419, compound

Product 2

HCID 7914Diisopropyl EtherHCID 22349452HCID 22349452, compoundYield 132.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 23 miligrams of 2-(2-Ethoxy-ethyl)-5-(4-hydroxy-phenoxy)-2,3-dihydro-isoindol-1-one (0.07 mmol), 5-bromo-5-(2-methoxy-ethyl)-pyrimidine-2,4,6-trione (0.021 grams, 0.08 mmol), 1,5,7-triazabicyclo[4.4.0]dec-5-ene bound to polystyrene (0.087 grams) and acetonitrile (0.5 mL) was shaken for 18 hours at room temperature. The mixture was treated with a solution of acetic acid in methanol (1:4 v/v), shaken for 20 minutes, and was filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica gel chromatography using 5% methanol in methylene chloride as eluant. Trituration of the purified product with iso-propyl ether afforded 5-(4-[2-(2-Ethoxy-ethyl)-1-oxo-2,3-dihydro-1H-isoindol-5-yloxy]-phenoxy)-5-(2-methoxy-ethyl)-pyrimidine-2,4,6-trione (0.023 grams) as a colorless solid. MS: 498.5 [M+H]+; 496.5 [M−H]−

Workup

  1. stirringshaken for 20 minutes
  2. filtrationwas filtered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6d29c90e74cf4d428720e0a823d3ee6c
Source dataset
uspto-grants-2005_07
Patent number
US06919332B2

Reaction notes

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