1,2-Dimethoxyethane → N-(4-(2-pyrimidinyl)phenyl)-2,2-dimethylpropanamide

HRID 1767630Notes

Reaction equation

HRID 1767630 reaction equation
[CH3:1][C:2]([CH3:16])([CH3:15])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9](B(O)O)=[CH:8][CH:7]=1)=[O:4].Cl[C:18]1[N:23]=[CH:22][CH:21]=[CH:20][N:19]=1.COCCOC>C([O-])([O-])=O.[Na+].[Na+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:19]1[CH:20]=[CH:21][CH:22]=[N:23][C:18]=1[C:9]1[CH:10]=[CH:11][C:6]([NH:5][C:3](=[O:4])[C:2]([CH3:16])([CH3:15])[CH3:1])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 744042-ChloropyrimidineHCID 223240854-Pivalamidophenylboronic acid

Product 1

HCID 22323983N-(4-(2-pyrimidinyl)phenyl)-2,2-dimethylpropanamideYield 85%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 10340Sodium CarbonateSolvent2×

Procedure

A mixture of 4-((2,2-dimethylpropanoyl)amino)phenylboronic acid (2.0 g, 9 mmol), 2-chloropyrimidine (0.8 g, 7 mmol), Pd(PPh3)2Cl2 (100 mg, 2 mol %) 1,2-dimethoxyethane (40 ml) and Na2CO3 (2M, 7 ml, 14 mmol) were refluxed under N2 for 5 h. The mixture was diluted with 10% Na2CO3 (20 ml) and extracted with EtOAc (3×50 ml). The organic layer was dried (Na2SO4) and the solvent was removed in vacuo. The crude product was recrystallised from MeOH/water (1:1) yielding 0.52 g (85%) of N-(4-(2-pyrimidinyl)phenyl)-2,2-dimethylpropanamide as colorless crystals.

Workup

  1. temperaturewere refluxed under N2 for 5 h
  2. extractionextracted with EtOAc (3×50 ml)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customthe solvent was removed in vacuo
  5. customThe crude product was recrystallised from MeOH/water (1:1)

Sources & evidence

ORD record
ord-f0e7f6e2dc3f43a098b1fbd70ce97d84
Source dataset
uspto-grants-2007_06
Patent number
US07235548B2

Reaction notes

Loading…