Lithium Hydroxide → [2-[2-(2,4-Difluorophenyl)ethyl]-4-oxopyrido[2,3-d]pyrimidin-1(4H)-yl]acetic acid
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]1[N:16]([CH2:17][C:18]([O:20]CC)=[O:19])[C:15]2[N:23]=[CH:24][CH:25]=[CH:26][C:14]=2[C:13](=[O:27])[N:12]=1.[OH-].[Li+]>C(O)C.O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]1[N:16]([CH2:17][C:18]([OH:20])=[O:19])[C:15]2[N:23]=[CH:24][CH:25]=[CH:26][C:14]=2[C:13](=[O:27])[N:12]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
Ethyl [2-[2-(2,4-difluorophenyl)ethyl]-4-oxopyrido[2,3-d]pyrimidin-1(4H)-yl]acetate (Int. C1) (32.76 g, 1 equiv) was dissolved in ethanol (350 ml) and water (70 ml), cooled in ice, then aqueous lithium hydroxide (2M solution, 43.42 ml, 0.99 equiv) was added. Stirring was continued for 2 h at room temperature. The solution was concentrated in vacuo and the residue was redissolved in water (700 ml) and saturated aqueous sodium bicarbonate (50 ml), then washed with ethyl acetate (200 ml). The aqueous layer was acidified to pH 2 with 2M hydrochloric acid, and the precipitate was filtered off, washed with ice water (50 ml) and dried in vacuo (50° C., 16 h) to obtain the desired product (23.2 g).
Workup
- concentrationThe solution was concentrated in vacuo
- dissolutionthe residue was redissolved in water (700 ml)
- washsaturated aqueous sodium bicarbonate (50 ml), then washed with ethyl acetate (200 ml)
- filtrationthe precipitate was filtered off
- washwashed with ice water (50 ml)
- customdried in vacuo (50° C., 16 h)
Sources & evidence
- ORD record
- ord-a6546255f26047f882242b66e906c1ec
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962633B2
Reaction notes
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