HCID 35475094, compound → HCID 1132958, compound

HRID 525065Notes

Reaction equation

HRID 525065 reaction equation
[CH2:1]([C:3]1[S:22][C:6]2[N:7]=[CH:8][N:9]=[C:10]([N:11]3[CH2:16][CH2:15][CH:14]([C:17]([O:19]CC)=[O:18])[CH2:13][CH2:12]3)[C:5]=2[CH:4]=1)[CH3:2]>[OH-].[NH4+]>[CH2:1]([C:3]1[S:22][C:6]2[N:7]=[CH:8][N:9]=[C:10]([N:11]3[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=[O:18])[CH2:13][CH2:12]3)[C:5]=2[CH:4]=1)[CH3:2]

Participants

3

Reactant 1

HCID 35475094HCID 35475094, compound

Product 1

HCID 1132958HCID 1132958, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

A solution of ethyl 1-[6-ethylthieno[2,3-d]pyrimidin-4-yl]piperidine-4-carboxylate (1.4 g, 4.38 mmol, 1.00 equiv) in ammonium hydroxide (50 mL) was heated to reflux for 12 hrs. The reaction mixture was cooled. The resulting mixture was concentrated under vacuum and dissolved in 20 ml of aqueous hydrogen chloride (12 N) and concentrated again to give 950 mg (crude) of 1-[6-ethylthieno[2,3-d]pyrimidin-4-yl]piperidine-4-carboxylic acid as a yellow solid.

Workup

  1. temperatureto reflux for 12 hrs
  2. temperatureThe reaction mixture was cooled
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. dissolutiondissolved in 20 ml of aqueous hydrogen chloride (12 N)
  5. concentrationconcentrated again

Sources & evidence

ORD record
ord-ad2a47a3668d41c3aa409d91a4fe6e23
Source dataset
uspto-grants-2016_05
Patent number
US09340554B2

Reaction notes

Loading…