Cesium carbonate → HCID 58446817, compound

HRID 1958341Notes

Reaction equation

HRID 1958341 reaction equation
Br.[NH2:2][C:3]1[CH:8]=[CH:7][N:6]2[CH:9]=[C:10]([C:12]3[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=3)[N:11]=[C:5]2[N:4]=1.[F:19][CH2:20]OS(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[F:19][CH2:20][O:18][C:14]1[CH:13]=[C:12]([C:10]2[N:11]=[C:5]3[N:4]=[C:3]([NH2:2])[CH:8]=[CH:7][N:6]3[CH:9]=2)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 13862289Fluoromethyl 4-methylbenzenesulfonateHCID 673879503-(7-Aminoimidazo[1,2-a]pyrimidin-2-yl)phenol hydrobromide

Product 1

HCID 58446817HCID 58446817, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

In a sealed tube 3-(7-aminoimidazo[1,2-a]pyrimidin-2-yl)phenol hydrobromide (260 mg, 0.85 mmol) was combined in DMF (3 ml) to give a brown solution. Toluene-4-sulfonic acid fluoromethyl ester (249 mg, 1.22 mmol; CAS Nr. 114435-86-8) was dissolved in DMF and added. Cs2CO3 (527 mg, 1.62 mmol) was added. The reaction mixture was heated under argon to 70° C. for 9 h, then stirring was continued overnight at RT. The reaction mixture was diluted with H2O (30 ml) and extracted with EtOAc (3×30 ml). The combined organic layers were dried (MgSO4) and concentrated under vacuum and the crude product was purified by flash chromatography (50 g SiO2, DCM/MeOH/NH3aq. 140:10:1). The title compound (105 mg, 48%) was obtained as a yellow solid.

Workup

  1. customto give a brown solution
  2. additionadded
  3. extractionextracted with EtOAc (3×30 ml)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated under vacuum
  6. customthe crude product was purified by flash chromatography (50 g SiO2, DCM/MeOH/NH3aq. 140:10:1)

Sources & evidence

ORD record
ord-a8968c8774b84a1f8995ac1bd3ae0b79
Source dataset
uspto-grants-2013_04
Patent number
US08410117B2

Reaction notes

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