Sodium;3-oxidodioxaborirane;tetrahydrate → HCID 89823887, compound

HRID 518789Notes

Reaction equation

HRID 518789 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[C:14]2[N:15]=[C:16]([S:19][CH3:20])[N:17]=[CH:18][C:13]=2[S:12][C:11]=1[C:21]([O:23][CH3:24])=[O:22])[CH3:2].B1([O-])OO1.[OH2:29].[OH2:30].O.O.[Na+]>C(O)(=O)C.O>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[C:14]2[N:15]=[C:16]([S:19]([CH3:20])(=[O:30])=[O:29])[N:17]=[CH:18][C:13]=2[S:12][C:11]=1[C:21]([O:23][CH3:24])=[O:22])[CH3:2]

Participants

5

Reactant 2

HCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrateHCID 89823781Thieno[3,2-d]pyrimidine-6-carboxylic acid, 7-(2-ethoxyphenyl)-2-(methylthio)-, methyl ester

Product 1

HCID 89823887HCID 89823887, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 330 mg of methyl 7-(2-ethoxyphenyl)-2-(methylsulfanyl)thieno[3,2-d]pyrimidine-6-carboxylate, prepared by analogy to the method described in example 4, and 634 mg of sodium perborate tetrahydrate in 15 ml of acetic acid is microwave-heated at 70° C. in a sealed tube for 1 h 30. The mixture is diluted with 5 volumes of water and the resulting precipitate is filtered off and washed with water. The solid is taken up with dichloromethane and 100 ml of a solution of sodium thiosulfate. The pH is adjusted to pH 8-9 by adding solid potassium carbonate and the aqueous phase is extracted with dichloromethane. The organic phases are dried over magnesium sulfate, filtered, and then concentrated under vacuum. This crude is purified on 40 g of silica, elution being carried out with dichloromethane, so as to obtain 296 mg of methyl 7-(2-ethoxyphenyl)-2-(methylsulfonyl)thieno[3,2-d]pyrimidine-6-carboxylate in the form of a yellow solid.

Workup

  1. customprepared by analogy to the method
  2. filtrationthe resulting precipitate is filtered off
  3. washwashed with water
  4. additionby adding solid potassium carbonate
  5. extractionthe aqueous phase is extracted with dichloromethane
  6. dry with materialThe organic phases are dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThis crude is purified on 40 g of silica, elution

Sources & evidence

ORD record
ord-5690f53990544f54ace01b2bca13e279
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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