Water → HCID 86697949, compound

HRID 518782Notes

Reaction equation

HRID 518782 reaction equation
[CH3:1][S:2]([C:5]1[N:6]=[CH:7][C:8]2[S:13][C:12]([C:14]([O:16][CH3:17])=[O:15])=[C:11](OS(C(F)(F)F)(=O)=O)[C:9]=2[N:10]=1)(=[O:4])=[O:3].[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>C1(C)C=CC=CC=1>[CH3:1][S:2]([C:5]1[N:6]=[CH:7][C:8]2[S:13][C:12]([C:14]([O:16][CH3:17])=[O:15])=[C:11]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:9]=2[N:10]=1)(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 86697950HCID 86697950, compound

Product 1

HCID 86697949HCID 86697949, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 253 mg of methyl 2-(methylsulfonyl)-7-{[(trifluoromethyl)sulfonyl]oxy}thieno[3,2-d]pyrimidine-6-carboxylate 5 (example 2), 110 mg of benzeneboronic acid, 392 mg of caesium carbonate and 49 mg of dichloropalladium(II)bis(diphenylphosphino)ferocene in 3.5 ml of toluene is heated at 90° C. for 30 min. The mixture is cooled and poured into water. The aqueous phase is extracted three times with dichloromethane. The organic phases are dried over magnesium sulfate, filtered, and then concentrated under vacuum. The residue is purified on 25 g of silica, elution being carried out with dichloromethane, so as to obtain 145 mg of methyl 2-(methylsulfonyl)-7-phenylthieno[3,2-d]pyrimidine-6-carboxylate in the form of a beige solid.

Workup

  1. temperatureThe mixture is cooled
  2. extractionThe aqueous phase is extracted three times with dichloromethane
  3. dry with materialThe organic phases are dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue is purified on 25 g of silica, elution

Sources & evidence

ORD record
ord-bcf5537f867640399a1e102941fd5995
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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