Methyl iodide → HCID 67257285, compound

HRID 1845878Notes

Reaction equation

HRID 1845878 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[Cl:19])[CH2:9][OH:10])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH3:22]I.[Cl-].[NH4+]>O1CCCC1>[Cl:19][C:13]1[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:12]=1[O:11][CH:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[N:7]=1)[CH2:9][O:10][CH3:22]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 67256425HCID 67256425, compound

Product 1

HCID 67257285HCID 67257285, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-aminopyrimidin-4-yl)-2-(2-chloro-4-fluorophenoxy)ethanol (21a) (185 mg) in dry tetrahydrofuran under nitrogen atmosphere was added sodium hydride (23 mg, 60% dispersion in oil) and the mixture was stirred at room temperature for 10 minutes, then methyl iodide (0.045 mL) was added. The mixture was stirred at room temperature for an additional for 45 minutes, poured onto sat aq ammonium chloride solution then extracted with ethyl acetate, washed with brine, dried over sodium sulfate and in vacuo. Purification by column chromatography eluting with 10 to 100% ether in heptane afforded the title compound (60 mg) as an oil that solidified upon standing, MS (ES): m/z 298 [M+H]+.

Workup

  1. stirringThe mixture was stirred at room temperature for an additional for 45 minutes
  2. additionpoured
  3. extractionthen extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate and in vacuo
  6. customPurification by column chromatography
  7. washeluting with 10 to 100% ether in heptane

Sources & evidence

ORD record
ord-a7b64636d876471893cb1051a6c10f5f
Source dataset
uspto-grants-2015_02
Patent number
US08952001B2

Reaction notes

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