Ethyl Acetate → 4-tert.-butyl-N-{6-[2-(ethanesulfonyl-methyl-amino)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-benzenesulfonamide

HRID 1358319Notes

Reaction equation

HRID 1358319 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](Cl)[N:18]=[CH:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH:29][CH2:30][CH2:31][N:32]([CH3:38])[S:33]([CH2:36][CH3:37])(=[O:35])=[O:34].C(OCC)(=O)C>C1COCC1>[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:29][CH2:30][CH2:31][N:32]([S:33]([CH2:36][CH3:37])(=[O:35])=[O:34])[CH3:38])[N:18]=[CH:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 18184242N-(2-hydroxyethyl)-N-methyl-ethanesulfonamideHCID 227294154-tert.-butyl-N-[6-chloro-5-(p-tolyl)4-pyrimidinyl]-benzene sulfonamide

Product 1

HCID 867590734-tert.-butyl-N-{6-[2-(ethanesulfonyl-methyl-amino)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-benzenesulfonamideYield 34.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

100 mg 4-tert.-butyl-N-[6-chloro-5-(p-tolyl)-4-pyrimidinyl]-benzene sulfonamide was dissolved in 5 ml dry THF. 162 mg of potassium-tert.-butylate and 200 mg of N-(2-hydroxyethyl)-N-methyl-ethanesulfonamide was added and the mixture was heated to reflux for 8 h then cooled to room temperature. Ethyl acetate was added and the precipitated side product was filtered off. The filtrate was concentrated in vacuo. The crude product was purified by column chromatography (silica gel; ethyl acetate) to give 45 mg of 4-tert.-butyl-N-{6-[2-(ethanesulfonyl-methyl-amino)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-benzenesulfonamide. LC-MS: tR=5.58 min, [M−1]−=545.54.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 8 h
  3. filtrationthe precipitated side product was filtered off
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe crude product was purified by column chromatography (silica gel; ethyl acetate)

Sources & evidence

ORD record
ord-514d1b28a69341c28f41b8bd3ee2e984
Source dataset
uspto-grants-2003_07
Patent number
US06596719B1

Reaction notes

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