Sodium hydride → HCID 58459086, compound

HRID 408822Notes

Reaction equation

HRID 408822 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[NH:11][C:12]2[C:17]([N:18]=1)=[C:16]([N:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH3:26])[CH2:21][CH2:20]1)[N:15]=[C:14]([CH3:27])[N:13]=2.[CH3:28][O:29][CH2:30]Br>O1CCCC1>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]([CH2:28][O:29][CH3:30])[C:12]2[C:17]([N:18]=1)=[C:16]([N:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH3:26])[CH2:21][CH2:20]1)[N:15]=[C:14]([CH3:27])[N:13]=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 83093Bromomethyl methyl etherHCID 178462714HCID 178462714, compound

Product 1

HCID 58459086HCID 58459086, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

Add sodium hydride (0.031 g, 0.0013 mol) to a solution of 8-(2-chlorophenyl)-6-(4-ethylpiperazin-1-yl)-2-methyl-9H-purine (0.233 g, 0.00065 mol) in dry tetrahydrofuran (20 mL) at 0° C. Stir the reaction mixture for 15 min, then cool to −30° C. and add bromomethyl methyl ether (0.081 g, 0.00065 mol). Warm the reaction mixture to room temperature and stir for one hour. Quench the reaction mixture with water, remove the tetrahydrofuran by evaporation and then extract the reaction mixture with dichloromethane. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate to give the residue. Purify the residue through preparative reverse phase HPLC (X-Bridge column, 5 mM NH4OAc/acetonitrile) to give the title compound (0.029 g). ES/MS m/z 401 (M+1).

Workup

  1. temperatureWarm the reaction mixture to room temperature
  2. stirringstir for one hour
  3. customQuench the reaction mixture with water
  4. customremove the tetrahydrofuran
  5. customby evaporation
  6. extractionextract the reaction mixture with dichloromethane
  7. dry with materialDry the organic layer over anhydrous sodium sulfate
  8. filtrationfilter
  9. concentrationconcentrate
  10. customto give the residue
  11. customPurify the residue through preparative reverse phase HPLC (X-Bridge column, 5 mM NH4OAc/acetonitrile)

Sources & evidence

ORD record
ord-0b5d9b03f5c84851a3ade6990fd75ae6
Source dataset
uspto-grants-2014_06
Patent number
US08759360B2

Reaction notes

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