Sodium Hydroxide → 2-(4,6-Dimethyl-5-nitropyrimidine-2-ylamino)acetic acid
Reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[N:5]=[C:4]([NH:12][CH2:13][C:14]([O:16]CC)=[O:15])[N:3]=1.[OH-].[Na+]>O1CCOCC1>[CH3:11][C:6]1[C:7]([N+:8]([O-:10])=[O:9])=[C:2]([CH3:1])[N:3]=[C:4]([NH:12][CH2:13][C:14]([OH:16])=[O:15])[N:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Compound 10 (80 mg) was suspended in 1,4-dioxane (1.5 mL) and a 2N aqueous sodium hydroxide solution (1.5 mL) was added at room temperature (20 to 30° C.). The mixture was stirred at room temperature (20 to 30° C.) for 8 hours. Subsequently, the mixture was washed with diethyl ether. While the reaction mixture was cooled, a 2N aqueous HCl solution was added portionwise to neutralize the mixture to a pH of 3. The mixture was extracted twice with chloroform and the organic layer was concentrated under reduced pressure to give 52 mg (75% yield) of the desired product as a pale yellow amorphous.
Workup
- washSubsequently, the mixture was washed with diethyl ether
- temperatureWhile the reaction mixture was cooled
- additiona 2N aqueous HCl solution was added portionwise
- extractionThe mixture was extracted twice with chloroform
- concentrationthe organic layer was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-73840c9e39d24b83b73ea951f2ea1fe9
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08592435B2
Reaction notes
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