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 1641361Notes

Reaction equation

HRID 1641361 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-7d21ec3bddfb4f5e9fb4b2b369f909e4
Source dataset
uspto-grants-2012_02
Patent number
US08114878B2

Reaction notes

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