Potassium tert-butoxide → 2-Phenyl-ethenesulfonic acid {6-[2-(4-bromo-phenoxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amide

HRID 965631Notes

Reaction equation

HRID 965631 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].BrC1C=CC(O[C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=2)=CC=1.CC(C)([O-])C.[K+].Cl[C:27]1[N:32]=[CH:31][N:30]=[C:29]([NH:33][S:34]([CH:37]=[CH:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)(=[O:36])=[O:35])[C:28]=1[C:45]1[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][CH:46]=1>COCCOC>[Br:19][C:16]1[CH:15]=[CH:14][C:13]([O:3][CH2:2][CH2:1][O:4][C:27]2[N:32]=[CH:31][N:30]=[C:29]([NH:33][S:34]([CH:37]=[CH:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)(=[O:35])=[O:36])[C:28]=2[C:45]2[CH:46]=[CH:47][C:48]([CH3:51])=[CH:49][CH:50]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 738818642-Phenyl-ethenesulfonic acid [6-chloro-5-p-tolyl-pyrimidin-4-yl]-amideHCID 86590291Ethyleneglycol mono-(4-bromo-phenyl)-ether

Product 1

HCID 670148102-Phenyl-ethenesulfonic acid {6-[2-(4-bromo-phenoxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amideYield 61.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Ethyleneglycol-mono-(4-bromo-phenyl)-ether (112 mg) was dissolved in 1,2-dimethoxyethane (5 ml) and potassium tert.-butoxide (50 mg) was added and stirring continued for 1 h, followed by the addition of 2-phenyl-ethenesulfonic acid [6-chloro-5-p-tolyl-pyrimidin-4-yl]-amide (100 mg) and stirring was continued at 80° C. for 24 h. The reaction mixture was evaporated to dryness, water (20 ml) was added followed by acidification with 10% citiric acid and extraction with ethyl acetate (2×, 20 ml). The combined organic layers were dried over sodium sulfate and the solvent was evaporated. The crude product was recrystallized from 2-propanol and 2-phenyl-ethenesulfonic acid {6-[2-(4-bromo-phenoxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amide (90 mg) was obtained as a white powder; tR=6.12 (LC); [M−H]+=565.75 (ES−).

Workup

  1. stirringstirring
  2. waitwas continued at 80° C. for 24 h
  3. customThe reaction mixture was evaporated to dryness, water (20 ml)
  4. additionwas added
  5. extractionfollowed by acidification with 10% citiric acid and extraction with ethyl acetate (2×, 20 ml)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. customthe solvent was evaporated
  8. customThe crude product was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-276529d9371742afb46517dd44389699
Source dataset
uspto-grants-2005_10
Patent number
US06951856B2

Reaction notes

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