Hydrochloric Acid → 3-{1-[5-oxo-4-(tetrahydropyran-4-ylamino)-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-2-yl]-piperidin-4-yl}-benzoic acid

HRID 405943Notes

Reaction equation

HRID 405943 reaction equation
[O:1]=[S:2]1[C:10]2[C:9]([NH:11][CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:8][C:7]([N:18]3[CH2:23][CH2:22][CH:21]([C:24]4[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=4)[C:27]([O:29]C)=[O:28])[CH2:20][CH2:19]3)=[N:6][C:5]=2[CH2:4][CH2:3]1.[OH-].[Na+].Cl>CO>[O:1]=[S:2]1[C:10]2[C:9]([NH:11][CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:8][C:7]([N:18]3[CH2:19][CH2:20][CH:21]([C:24]4[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=4)[C:27]([OH:29])=[O:28])[CH2:22][CH2:23]3)=[N:6][C:5]=2[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25271275HCID 25271275, compound

Product 1

HCID 581175463-{1-[5-oxo-4-(tetrahydropyran-4-ylamino)-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-2-yl]-piperidin-4-yl}-benzoic acidYield 60.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1.3 g methyl 3-{1-[5-oxo-4-(tetrahydropyran-4-ylamino)-6,7-dihydro-5H-5λ4-thieno[3,2-d]pyrimidin-2-yl]-piperidin-4-yl}-benzoate are placed in 24.6 ml of methanol, then 9.2 ml of a 1 N NaOH solution are added. The reaction mixture is stirred at ambient temperature until there is no further reaction, then combined with a 1 N HCl solution. The methanol is spun off and the precipitated solid is suction filtered. The product is purified by preparative HPLC (method B). 760 mg product are obtained as a solid.

Workup

  1. customno further reaction
  2. filtrationfiltered
  3. customThe product is purified by preparative HPLC (method B)

Sources & evidence

ORD record
ord-4dcaeed60c004b8aa888806d5d7cf4b7
Source dataset
uspto-grants-2014_06
Patent number
US08754073B2

Reaction notes

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