Diethyl Ether → HCID 67195988, compound

HRID 550799Notes

Reaction equation

HRID 550799 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[CH2:31][S:30][CH2:29][C:16]=3[N:17]=[C:18]([C:20]3[CH:25]=[C:24]([F:26])[C:23]([Cl:27])=[CH:22][C:21]=3[F:28])[N:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:32].O1CCOCC1.[OH-].[Na+].C(OCC)C>CO>[ClH:27].[ClH:32].[Cl:27][C:23]1[C:24]([F:26])=[CH:25][C:20]([C:18]2[N:19]=[C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[C:15]3[CH2:31][S:30][CH2:29][C:16]=3[N:17]=2)=[C:21]([F:28])[CH:22]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 204431481,4-Dioxane hydrochloride2×HCID 67197650HCID 67197650, compound

Product 1

HCID 67195988HCID 67195988, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 503 mg of 1-tert-butoxycarbonyl-4-[2-(4-chloro-2,5-difluorophenyl)-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazine, 2 ml of MeOH, and 6 ml of 4M HCl-dioxane solution was stirred at ambient temperature for 1 hour. To the reaction mixture were added 15 ml of 1M aqueous sodium hydroxide and 2 ml of diethyl ether, and the precipitate was collected by filtration, washed with water and then diethyl ether, and dried under reduced pressure. The solid obtained was dissolved in 5 ml of MeOH, here was added 2 ml of 4M HCl-dioxane solution, and the solvent was then distilled off under reduced pressure. The residue obtained was washed with EtOH-EtOAc and dried under reduced pressure to yield 423 mg of 2-(4-chloro-2,5-difluorophenyl)-4-piperazin-1-yl-5,7-dihydrothieno[3,4-d]pyrimidine dihydrochloride.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with water
  3. dry with materialdiethyl ether, and dried under reduced pressure
  4. customThe solid obtained
  5. distillationthe solvent was then distilled off under reduced pressure
  6. customThe residue obtained
  7. washwas washed with EtOH-EtOAc
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-d42a265d906546aeb203200b1e76d0d5
Source dataset
uspto-grants-2011_05
Patent number
US07947690B2

Reaction notes

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