Phenol → HCID 19934777, compound

HRID 37102

Reaction equation

HRID 37102 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=3[Cl:30])=[C:19]([CH2:31]Cl)[N:18]=[C:17]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:39]1([O-:45])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.[Na+].C1(O)C=CC=CC=1.[OH-].[Na+]>CC(C)=O.O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=3[Cl:30])=[C:19]([CH2:31][O:45][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:18]=[C:17]([N:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)[N:16]=2)(=[O:12])=[O:13])=[CH:7][CH:6]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 996PhenolHCID 14798Sodium HydroxideHCID 4445035Phenolate SodiumHCID 199347554-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-chloromethyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamide

Product 1

HCID 19934777HCID 19934777, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

0.145 g of 4-tert.-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-chloromethyl-2-(morpholin-4-yl)-pyrimidin-4-yl]benzenesulphonamide (Example 4) in 3 ml of acetone was added to a sodium phenolate solution from 0,024 g of phenol and 0.06 g of NaOH in 2 ml of acetone and 1 ml of water. The reaction mixture was stirred at 80° C. under argon for 48 hours. Thereafter, the acetone was distilled off and the residue was partitioned between chloroform and water. The chloroform phase was washed with water, dried over sodium sulphate and the solvent was distilled off. The residue was chromatographed over silica gel with chloroform. 0.07 g of 4-tert.-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-2-morpholin-4-yl-6-phenoxymethyl-pyrimidin-4-yl]benzenesulphonamide, MS: M=639, was obtained.

Workup

  1. distillationThereafter, the acetone was distilled off
  2. customthe residue was partitioned between chloroform and water
  3. washThe chloroform phase was washed with water
  4. dry with materialdried over sodium sulphate
  5. distillationthe solvent was distilled off
  6. customThe residue was chromatographed over silica gel with chloroform

Sources & evidence

ORD record
ord-d0aa28ba710c4f8cadc523ef1d3f73ae
Source dataset
uspto-grants-1995_05
Patent number
US05420129

Linked notes

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