Reaction #2365

Reaction equation

ammonium chloride

2-chloropyrimidine

Compound B

4-tert-butyl-N-{6-(2-hydroxyethylamino)-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide

sodium hydride

→

4-tert-butyl-N-[5-(3-methoxyphenoxy)-6-{2-(pyrimidin-2-yloxy)ethylamino}pyrimidin-4-yl]benzenesulfonamide

Yield 92.5%

Solvents

dimethylacetamide

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate
2. 2
   WashThe ethyl acetate layer is washed
3. 3
   Otherdried
4. 4
   Otherevaporated
5. 5
   Otherto remove the solvent
6. 6
   OtherThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=20:1)
7. 7
   Othercrystallized from chloroform/diisopropyl ether

Procedure

To a solution of Compound B (116 mg) obtained in Example 19-(1) in dimethylacetamide (2 ml) is added sodium hydride (60% dispersion-type, 33 mg), and thereto is added 2-chloropyrimidine (40 mg). The reaction solution is stirred at room temperature overnight, and the mixture is treated with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform/methanol=20:1), and crystallized from chloroform/diisopropyl ether to give 4-tert-butyl-N-[5-(3-methoxyphenoxy)-6-{2-(pyrimidin-2-yloxy)ethylamino}pyrimidin-4-yl]benzenesulfonamide (125 mg) as crystals.

Source