Toluene → HCID 9801412, compound

HRID 2300838Notes

Reaction equation

HRID 2300838 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[C:12](Cl)[N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O.C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCO>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[C:12]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[CH3:26])[N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 86758759HCID 86758759, compound

Product 1

HCID 9801412HCID 9801412, compoundYield 48.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-[(S)-1-phenylethylamino]-4-[benzimidazol-1-yl]-6-chloropyrimidine (30 mg) and 2-methylphenyboronic acid (18 mg) in 10:1 toluene:EtOH was added 1M Na2CO3 (0.215 mL) and Pd(PPh3)4 (5 mg). The resulting mixture was heated and maintained at reflux for 9 h, then cooled and filtered through MgSO4. The filtrate was concentrated under reduced pressure and purified by preparative thin layer chromatography (1:50 EtOAc:CH2Cl2) to give 17 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 8.58 (br s, 1H); 7.85-7.3 (m, 13H); 6.9 (s, 1H); 5.9 (br s, 1H); 5.25 (br s, 1H); 2.45 (br s, 3H); 1.7 (d, J=7.1 Hz, 3H). Mass spectrum (CI) 406.3 (M+1).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperaturemaintained
  3. temperatureat reflux for 9 h
  4. temperaturecooled
  5. filtrationfiltered through MgSO4
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by preparative thin layer chromatography (1:50 EtOAc:CH2Cl2)

Sources & evidence

ORD record
ord-85d861746b2f46969e898534fdf63af8
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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