Hydrochloric Acid → HCID 69071303, compound

HRID 225489Notes

Reaction equation

HRID 225489 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Cl:11][C:12]1[C:17]([F:18])=[CH:16][C:15]([C:19]2[N:20]=[C:21]([N:28]3[CH2:33][CH2:32][NH:31][CH:30]([C:34](OCC)=[O:35])[CH2:29]3)[C:22]3[S:27][CH:26]=[CH:25][C:23]=3[N:24]=2)=[C:14]([F:39])[CH:13]=1.[ClH:40].[OH-].[Na+].Cl.O1CCOCC1>C1COCC1>[ClH:11].[ClH:40].[Cl:11][C:12]1[C:17]([F:18])=[CH:16][C:15]([C:19]2[N:20]=[C:21]([N:28]3[CH2:33][CH2:32][NH:31][CH:30]([CH2:34][OH:35])[CH2:29]3)[C:22]3[S:27][CH:26]=[CH:25][C:23]=3[N:24]=2)=[C:14]([F:39])[CH:13]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 204431481,4-Dioxane hydrochlorideHCID 21225700DiisobutylaluminumhydrideHCID 69070115HCID 69070115, compound

Product 1

HCID 69071303HCID 69071303, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

3.65 ml of THF solution with 1.0M diisobutylaluminum hydride was added dropwise under ice cooling into a mixture of 400 mg of ethyl 4-[2-(4-chloro-2,5-difluorophenyl)thieno[3,2-d]pyrimidine-4-yl]piperazine-2-carboxylate and 10 ml of THF and the resultant was stirred for 3 hours at room temperature. After 10 ml of 1M HCl aq was added to the reaction mixture and stirred for 10 minutes at room temperature, 20 ml of 1M NaOH aq was added and extracted with chloroform. After the organic layer was 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 an oily substance. After the obtained oily substance was dissolved in 10 ml of THF and 1 ml of 4M HCl-dioxane solution was added, the resultant was concentrated under reduced pressure to give a solid. This solid washed with EtOH-ether to give 60 mg of {4-[2-(4-chloro-2,5-difluorophenyl)thieno[3,2-d]pyrimidine-4-yl]piperazine-2-yl}methanol dihydrochloride.

Workup

  1. stirringstirred for 10 minutes at room temperature
  2. extractionextracted with chloroform
  3. dry with materialAfter the organic layer was dried 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 an oily substance
  7. concentrationthe resultant was concentrated under reduced pressure
  8. customto give a solid
  9. washThis solid washed with EtOH-ether

Sources & evidence

ORD record
ord-e4496eaa8db248de9003204aac596465
Source dataset
uspto-grants-2009_07
Patent number
US07557112B2

Reaction notes

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