Cesium carbonate → HCID 69100596, compound

HRID 1907781Notes

Reaction equation

HRID 1907781 reaction equation
[Cl-].[F:2][C:3]([F:18])([F:17])[C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][C@@H:14]3[CH2:16][C@H:11]2[CH2:12][NH2+:13]3)[CH:7]=[CH:8][CH:9]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS([C:29]1[N:34]=[CH:33][C:32]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:31][N:30]=1)(=O)=O>CN(C=O)C.O.C(OCC)(=O)C>[F:18][C:3]([F:2])([F:17])[C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][C@@H:14]3[CH2:16][C@H:11]2[CH2:12][N:13]3[C:29]2[N:30]=[CH:31][C:32]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:33][N:34]=2)[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 254889Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylateHCID 67006616HCID 67006616, compound

Product 1

HCID 69100596HCID 69100596, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 558 (500 mg, 1.794 mmol) and cesium carbonate (1461 mg, 4.49 mmol) were suspended in DMF (5 mL) to give a yellow suspension. Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate (496 mg, 2.153 mmol) was then added and the reaction was stirred at room temperature for 3 days. The mixture was diluted with water and ethyl acetate. The organic layer was washed twice with water then brine and dried with MgSO4. The solvent was removed in vacuo and the residue was purified by column chromatography (25-50% EtOAc in Hexanes) to obtain compound 559 as a white solid (313 mg, 45%). LRMS: 392.1 (found) 393.2 (MH)+.

Workup

  1. customto give a yellow suspension
  2. washThe organic layer was washed twice with water
  3. dry with materialbrine and dried with MgSO4
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by column chromatography (25-50% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-985375c34e664ebe944e70162042de62
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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