Cesium carbonate → HCID 86732453, compound

HRID 1776427Notes

Reaction equation

HRID 1776427 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[N:19]=[C:18]([NH:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[C:17]([O:27][CH3:28])=[CH:16][N:15]=2)=[N:6]1.[C:33](=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1=O>[F:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[N:19]=[C:18]([N:20]([CH3:33])[C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[C:17]([O:27][CH3:28])=[CH:16][N:15]=2)=[N:6]1

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 71553617HCID 71553617, compound

Product 1

HCID 86732453HCID 86732453, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
190 °C

Procedure

135 mg of 2-[1-(2-fluorobenzyl)-1H-indazol-3-yl]-5-methoxy-N-(pyridin-4-yl)-pyrimidin-4-amine (2-18-1, 0.316 mmol, 1. eq.) were dissolved in 3 ml of 1-methylpyrrolidin-2-one and 514 mg of cesium carbonate (1.58 mmol, 5 eq.) were added. The reaction mixture was stirred at 190° C. bath temperature for 18 hours. After cooling at room temperature the mixture was partitioned between water and butan-2-one. The phases were separated and the aqueous layer was extracted twice with butan-2-one. The combined organic layers were washed with brine and dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography and preparative TLC to yield 10.9 mg (0.02 mmol, 7.2%) of the analytically pure target compound.

Workup

  1. temperatureAfter cooling at room temperature the mixture
  2. customwas partitioned between water and butan-2-one
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted twice with butan-2-one
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography and preparative TLC
  9. customto yield 10.9 mg (0.02 mmol, 7.2%) of the analytically pure target compound

Sources & evidence

ORD record
ord-d052ee2ab66748c9841fd7ac1a166185
Source dataset
uspto-grants-2016_02
Patent number
US09265763B2

Reaction notes

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