Carbon Dioxide → HCID 66673079, compound

HRID 225490Notes

Reaction equation

HRID 225490 reaction equation
[N:1]1([C:8]2[C:9]3[S:25][CH:24]=[CH:23][C:10]=3[N:11]=[C:12]([C:14]3[CH:19]=[C:18]([F:20])[C:17]([Cl:21])=[CH:16][C:15]=3[F:22])[N:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:26](=[O:28])=[O:27].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[N:1]1([C:8]2[C:9]3[S:25][C:24]([C:26]([OH:28])=[O:27])=[CH:23][C:10]=3[N:11]=[C:12]([C:14]3[CH:19]=[C:18]([F:20])[C:17]([Cl:21])=[CH:16][C:15]=3[F:22])[N:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 311Citric AcidHCID 66674077HCID 66674077, compound

Product 1

HCID 66673079HCID 66673079, compoundYield 14,181.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.32 ml of 1.59M n-butyllithium-hexane solution was added dropwise for 5 minutes at −78° C. into a mixture of 1.82 g of 4-azepane-1-yl-2-(4-chloro-2,5-difluorophenyl)thieno[3,2-d]pyrimidine and 40 ml of THF and stirred for 15 minutes. Approximately 50 g of crushed dry ice was added to the reaction mixture and the temperature subsequently raised to room temperature. 50 ml of 10% citric acid solution was added to the reaction mixture and extracted with EtOAc. After the organic layer washed with a saturated saline solution and dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform-MeOH) to give a foam-like substance. The foam-like substance was recrystallized from THF-acetonitrile to give 288 g of 4-azepane-1-yl-2-(4-chloro-2,5-difluorophenyl)thieno[3,2-d]pyrimidine-6-carboxylic acid.

Workup

  1. extractionextracted with EtOAc
  2. washAfter the organic layer washed with a saturated saline solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform-MeOH)
  6. customto give a foam-like substance
  7. customThe foam-like substance was recrystallized from THF-acetonitrile

Sources & evidence

ORD record
ord-8332963941de453fbf1d2ea7eeaab679
Source dataset
uspto-grants-2009_07
Patent number
US07557112B2

Reaction notes

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