Lithium hydroxide, monohydrate → (S)-2-Chloro-4-(1-(5-fluoropyridin-2-yl)ethylamino)pyrimidine-5-carboxylic acid
Reaction equation
O.[OH-].[Li+].[Cl:4][C:5]1[N:10]=[C:9]([NH:11][C@H:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][N:15]=2)[CH3:13])[C:8]([C:21]([O:23]CC)=[O:22])=[CH:7][N:6]=1>O.CO.O1CCCC1>[Cl:4][C:5]1[N:10]=[C:9]([NH:11][C@H:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][N:15]=2)[CH3:13])[C:8]([C:21]([OH:23])=[O:22])=[CH:7][N:6]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of lithium hydroxide monohydrate (633 mg, 15.09 mmol) in water (6 mL) was added to a solution of (S)-ethyl 2-chloro-4-(1-(5-fluoropyridin-2-yl)ethylamino)pyrimidine-5-carboxylate (Preparation 5a, 490 mg, 1.51 mmol) in a mixture of methanol (6 mL) and tetrahydrofuran (2 mL) and the reaction mixture was stirred at ambient temperature for 3 hours. The solvents were evaporated under reduced pressure and water was added to the resulting residue. The pH was then adjusted to ca. 6 with 2M aqueous hydrochloric acid and the aqueous suspension was extracted with diethyl ether (×3). The organic phase was washed with water and brine, dried (MgSO4), filtered and the solvent evaporated under reduced pressure to give the title compound (0.21 g, 41%) as a semi-solid.
Workup
- customThe solvents were evaporated under reduced pressure and water
- additionwas added to the resulting residue
- extractionthe aqueous suspension was extracted with diethyl ether (×3)
- washThe organic phase was washed with water and brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- customthe solvent evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-0aa9fc8918c040b49ae4f5c68af972d7
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09034311B2
Reaction notes
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