Hydrochloric Acid → 5-methyl-4-(2-(tetrahydro-2H-pyran-4-yloxy)pyridin-3-ylamino)thieno[2,3-d]pyrimidine-6-carboxylic acid
Reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([NH:11][C:12]3[C:13]([O:18][CH:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[N:14][CH:15]=[CH:16][CH:17]=3)=[N:8][CH:7]=[N:6][C:5]=2[S:4][C:3]=1[C:25]([O:27]C)=[O:26].CO.[OH-].[Na+].Cl>C(Cl)Cl>[CH3:1][C:2]1[C:10]2[C:9]([NH:11][C:12]3[C:13]([O:18][CH:19]4[CH2:20][CH2:21][O:22][CH2:23][CH2:24]4)=[N:14][CH:15]=[CH:16][CH:17]=3)=[N:8][CH:7]=[N:6][C:5]=2[S:4][C:3]=1[C:25]([OH:27])=[O:26]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Methyl 5-methyl-4-(2-(tetrahydro-2H-pyran-4-yloxy)pyridin-3-ylamino)thieno[2,3-d]pyrimidine-6-carboxylate (0.921 g, 2.30 mmol) was added into a solution of MeOH (8 mL) and 2M aqueous sodium hydroxide (2.0 mL). The reaction was stirred at 60° C. for two hours. The mixture was cooled to ambient temperature and acidified with concentrated hydrochloric acid. On addition of DCM a precipitate formed which was collected and washed with water. The product was purified by reverse phase preparative HPLC to yield off-white solid which was used in the next step without further purification.
Workup
- temperatureThe mixture was cooled to ambient temperature
- customformed which
- customwas collected
- washwashed with water
- customThe product was purified by reverse phase preparative HPLC
- customto yield off-white solid which
- customwas used in the next step without further purification
Sources & evidence
- ORD record
- ord-60e0b95182874829a36cabd52ab0f0dc
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08486953B2
Reaction notes
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