Cesium carbonate → HCID 66888334, compound

HRID 1893713Notes

Reaction equation

HRID 1893713 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([OH:18])[S:16][CH:17]=3)[C:10]([CH3:19])=[N:9]2)=[CH:5][CH:4]=1.Cl[C:23]1[N:28]=[CH:27][CH:26]=[CH:25][N:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O.[Cu]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([O:18][C:23]4[N:28]=[CH:27][CH:26]=[CH:25][N:24]=4)[S:16][CH:17]=3)[C:10]([CH3:19])=[N:9]2)=[CH:20][CH:21]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 744042-ChloropyrimidineHCID 178490772HCID 178490772, compound

Product 1

HCID 66888334HCID 66888334, compoundYield 18.2%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

According to Scheme 2, Step 5: A mixture of 4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl)thiazol-2-ol (0.99 mmol, 300 mg), 2-chloropyrimidine (0.99 mmol, 114 mg), copper (0.20 mmol, 12.6 mg) and cesium carbonate (2.99 mmol, 973 mg) in DMF (3.3 mL) was stirred at 160° C. under microwave conditions for 45 minutes. Then, the reaction mixture was diluted with EtOAc and was washed with water. The organic phase was dried over MgSO4, was filtered and was evaporated. The crude mixture was purified by flash chromatography over silica gel using cyclohexane/EtOAc (80:20 to 60:40) as eluent to yield 4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl)-2-(pyrimidin-2-yloxy)thiazole (0.18 mmol, 67 mg, 18%) as a yellow oil.

Workup

  1. washwas washed with water
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationwas filtered
  4. customwas evaporated
  5. customThe crude mixture was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-060d80d204b7470eafe8a8b83064d141
Source dataset
uspto-grants-2013_08
Patent number
US08513252B2

Reaction notes

Loading…