Cesium carbonate → HCID 86621088, compound

HRID 1620830Notes

Reaction equation

HRID 1620830 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[O:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH:16]([OH:21])[C:17]([F:20])([F:19])[F:18])=[CH:7][CH:6]=1)[CH3:3].[NH2:22][C:23]1[N:28]=[C:27](Cl)[CH:26]=[C:25]([Cl:30])[N:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>C(OCC)(=O)C>[Cl:30][C:25]1[CH:26]=[C:27]([O:21][CH:16]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:8]2[O:9][C:5]([CH2:4][N:2]([CH3:1])[CH3:3])=[CH:6][CH:7]=2)[C:17]([F:18])([F:20])[F:19])[N:28]=[C:23]([NH2:22])[N:24]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 655222-Amino-4,6-dichloropyrimidineHCID 66742833HCID 66742833, compound

Product 1

HCID 86621088HCID 86621088, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

The mixture of 1-[2-(5-dimethylaminomethyl-furan-2-yl)-phenyl]-2,2,2-trifluoro-ethanol (225 mg, 0.75 mmol), 2-amino-4,6-dichloro-pyrimidine (111 mg, 0.67 mmol), cesium carbonate (978 mg, 3.01 mmol) and 1,4-dioxane (3 ml) was heated at 110° C. overnight. The reaction mixture was cooled to room temperature; 10 ml of ethyl acetate was added. The mixture was then filtered through Celite, the filtrate was concentrated to give 110 mg of 4-chloro-6-{1-[2-(5-dimethylaminomethyl-furan-2-yl)-phenyl]2,2,2-trifluoro-ethoxy}-pyrimidin-2-ylamine, yield 87%.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe mixture was then filtered through Celite
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-18a16852b27046f9a68aac1c6548e1de
Source dataset
uspto-grants-2014_07
Patent number
US08772482B2

Reaction notes

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