Sodium hydride → HCID 69937907, compound

HRID 2401327Notes

Reaction equation

HRID 2401327 reaction equation
[OH:1][CH2:2][C:3]12[CH2:10][CH2:9][C:6]([C:11]3[NH:19][C:18]4[C:17](=[O:20])[N:16]([CH2:21][CH2:22][CH3:23])[C:15](=[O:24])[NH:14][C:13]=4[N:12]=3)([CH2:7][CH2:8]1)[CH2:5][CH2:4]2.[H-].[Na+].Br[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][N:29]=1>CN(C=O)C>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([O:1][CH2:2][C:3]23[CH2:8][CH2:7][C:6]([C:11]4[NH:19][C:18]5[C:17](=[O:20])[N:16]([CH2:21][CH2:22][CH3:23])[C:15](=[O:24])[NH:14][C:13]=5[N:12]=4)([CH2:9][CH2:10]2)[CH2:5][CH2:4]3)=[N:29][CH:30]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 8170982-Bromo-5-chloropyridineHCID 70656103HCID 70656103, compound

Product 1

HCID 69937907HCID 69937907, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 8-(4-hydroxymethyl-bicyclo[2.2.2]oct-1-yl)-1-propyl-3,7-dihydro-purine-2,6-dione (0.2 g, 0.60 mmol) in DMF (4 ml) was added NaH (60% dispersion in mineral oil, 0.079 g, 1.98 mmol) at room temperature followed by 2-bromo-5-chloro-pyridine and maintained at 120° C. overnight. Reaction mixture was concentrated under reduced pressure quenched with water and was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated under vacuum. The crude product was purified by column chromatography using 2% methanol in dichloromethane as solvent system.

Workup

  1. customReaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. customquenched with water
  4. extractionwas extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  6. concentrationconcentrated under vacuum
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-ad6652e7339b405e8cc566ea12a5e1b3
Source dataset
uspto-grants-2014_08
Patent number
US08796290B2

Reaction notes

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