Methanol → 4-tert-butyl-N-{6-[2-(5-ethynylpyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide

HRID 2298

Reaction equation

HRID 2298 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)=[C:19]([O:28][CH2:29][CH2:30][O:31][C:32]3[N:37]=[CH:36][C:35]([C:38]#[C:39][Si](C)(C)C)=[CH:34][N:33]=3)[N:18]=[CH:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].CO>[Cl-].[NH4+]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)=[C:19]([O:28][CH2:29][CH2:30][O:31][C:32]3[N:33]=[CH:34][C:35]([C:38]#[CH:39])=[CH:36][N:37]=3)[N:18]=[CH:17][N:16]=2)(=[O:12])=[O:13])=[CH:7][CH:6]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 196895234-tert-butyl-N-{6-[2-(5-trimethylsilylethynylpyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide

Product 1

HCID 196894594-tert-butyl-N-{6-[2-(5-ethynylpyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamideYield 85.3%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-tert-butyl-N-{6-[2-(5-trimethylsilylethynylpyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (667 mg), potassium carbonate (299 mg) and dry methanol (13 ml) is stirred at 0° C. for two hours, and diluted with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The organic layer is washed with water and brine, dried over sodium sulfate, and filtered. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=30:1) to give 4-tert-butyl-N-{6-[2-(5-ethynylpyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}-benzenesulfonamide (502 mg) as colorless crystalline powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated under reduced pressure
  6. customthe residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=30:1)

Sources & evidence

ORD record
ord-ef654fd56d444338b74762628d0ff15f
Source dataset
uspto-grants-1998_03
Patent number
US05728706

Linked notes

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