Sodium Hydroxide → 4-{4-[4-(3-chloro-phenylamino)-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-2-yl]-piperazin-1-yl}-benzoic acid

HRID 70113Notes

Reaction equation

HRID 70113 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:10]3[S:34](=[O:35])[CH2:33][CH2:32][C:11]=3[N:12]=[C:13]([N:15]3[CH2:20][CH2:19][N:18]([C:21]4[CH:31]=[CH:30][C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][CH:22]=4)[CH2:17][CH2:16]3)[N:14]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>CO.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:10]3[S:34](=[O:35])[CH2:33][CH2:32][C:11]=3[N:12]=[C:13]([N:15]3[CH2:16][CH2:17][N:18]([C:21]4[CH:31]=[CH:30][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=4)[CH2:19][CH2:20]3)[N:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59708453ethyl 4-{4-[4-(3-chloro-phenylamino)-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-2-yl]-piperazin-1-yl}-benzoate

Product 1

HCID 597083844-{4-[4-(3-chloro-phenylamino)-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-2-yl]-piperazin-1-yl}-benzoic acidYield 59.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

6.90 g ethyl 4-{4-[4-(3-chloro-phenylamino)-5-oxo-6,7-dihydro-5H-5λ4-thieno[3,2-d]pyrimidin-2-yl]-piperazin-1-yl}-benzoate and 70 ml of 1 molar sodium hydroxide solution are placed in 40 ml of methanol and 40 ml of tetrahydrofuran, then refluxed for 1.5 hours with stirring. The resulting solution is evaporated down, the residue is cooled and acidified slightly with 2 molar hydrochloric acid. The precipitate formed is suction filtered, washed and dried. The substance is stirred with ethyl acetate/methanol 9:1, suction filtered and dried. 3.90 g of the product are obtained as a powder.

Workup

  1. customThe resulting solution is evaporated down
  2. temperaturethe residue is cooled
  3. customThe precipitate formed
  4. filtrationfiltered
  5. washwashed
  6. customdried
  7. stirringThe substance is stirred with ethyl acetate/methanol 9:1, suction
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-c2dadef55a594e03ad88d4a913839656
Source dataset
uspto-grants-2014_09
Patent number
US08822474B2

Reaction notes

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