Sodium Carbonate → HCID 20594038, compound

HRID 1369415Notes

Reaction equation

HRID 1369415 reaction equation
Br[C:2]1[N:3]=[C:4]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[N:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:15])[N:8]=2)[CH:6]=1.C[Sn](C)(C)[C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1.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>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C:4]2[N:5]([C:7]3[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C@H:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH3:15])[N:8]=3)[CH:6]=[C:2]([C:31]3[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=3)[N:3]=2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 11128458Pyridine, 4-(trimethylstannyl)-HCID 20594053HCID 20594053, compound

Product 1

HCID 20594038HCID 20594038, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

4-Bromo-2-(4-fluorophenyl)-1-(2-[1-(S)-phenylethyl]amino-4-pyrimidyl)imidazole (1.0 g; 2.28 mmol), 4-trimethylstannylpyridine (660 mg; 2.74 mmol) and PdCl2(PPh3)2 (160 mg; 0.228 mmol) are dissolved in xylenes (23 ml) and refluxed for 4 h. The reaction mixture is poured on saturated Na2CO3 solution and extracted with ethyl acetate three times. The combined organic phases were dried over Na2SO4, filtered, evaporated to dryness and purified via SiO2 chromatography (TBME/MeOH/NH3conc 99/9/0.1) to yield the title compound as a yellow foam (780 mg; 68%).

Workup

  1. temperaturerefluxed for 4 h
  2. extractionextracted with ethyl acetate three times
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. custompurified via SiO2 chromatography (TBME/MeOH/NH3conc 99/9/0.1)

Sources & evidence

ORD record
ord-56f8f45a78a14cdaa1c10e0d4f3d98ab
Source dataset
uspto-grants-2003_06
Patent number
US06579874B2

Reaction notes

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