Sodium Hydroxide → 2-[6-Chloro-2-methyl-8-oxo-9-(4-isopropyl-2-methylthiophenyl)-8,9-dihydropurin-7-yl]acetic acid
Reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([CH3:11])[N:8]=[C:7]2[C:3]=1[N:4]([CH2:24][C:25]([O:27]CC)=[O:26])[C:5](=[O:23])[N:6]2[C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][C:13]=1[S:21][CH3:22].[OH-].[Na+]>CO.O>[Cl:1][C:2]1[N:10]=[C:9]([CH3:11])[N:8]=[C:7]2[C:3]=1[N:4]([CH2:24][C:25]([OH:27])=[O:26])[C:5](=[O:23])[N:6]2[C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:19])[CH3:20])=[CH:14][C:13]=1[S:21][CH3:22]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
In a mixed solvent of 3 ml of methanol and 1 ml of water, 0.83 g of ethyl 2-[6-chloro-2-methyl-8-oxo-9-(4-isopropyl-2-methylthiophenyl)-8 9-dihydropurin-7-yl]acetate was dissolved, and subsequently, 80 mg of sodium hydroxide was added thereto. The reaction mixture was stirred for 30 minutes at room temperature. Water was poured into the reaction mixture. The reaction mixture was extracted with chloroform. The extract was dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:chloroform—methanol=8:1) to yield 0.47 g of 2-[6-chloro-2-methyl-8-oxo-9-(4-isopropyl-2-methylthiophenyl)-8,9-dihydropurin-7-yl]acetic acid as an oil.
Workup
- extractionThe reaction mixture was extracted with chloroform
- dry with materialThe extract was dried over anhydrous sodium sulfate
- filtrationAfter the desiccant was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (eluent:chloroform—methanol=8:1)
Sources & evidence
- ORD record
- ord-d7170b378ca64c08b334ff02aaf37952
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06600038B1
Reaction notes
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