Sodium hydride → HCID 18619246, compound
Reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[C:12](Cl)=[N:13][C:14]([CH3:17])=[N:15][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:19]([O:23][CH3:24])(=[O:22])[CH2:20][OH:21]>O1CCCC1>[CH2:3]([O:10][C:11]1[C:12]([O:21][CH2:20][C:19]([O:23][CH3:24])=[O:22])=[N:13][C:14]([CH3:17])=[N:15][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
68 mg of sodium hydride was added to a mixture of 0.4 g of 5-benzyloxy-4-chloro-2-methylpyrimidine, 0.17 g of methyl glycolate and 3.4 ml of tetrahydrofuran at 0° C. The mixture was stirred at room temperature for 1 hour, then, the reaction solution was stirred for 30 minutes at 90° C. 18 mg of methyl glycolate was additionally added to this, and the mixture was stirred for 30 minutes at 90° C. The reaction solution was cooled to room temperature, then, poured into ice water, and extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid and saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.21 g of 5-benzyloxy-4-(methoxycarbonyl)methoxy-2-methylpyrimidine.
Workup
- stirringthe reaction solution was stirred for 30 minutes at 90° C
- stirringwas stirred for 30 minutes at 90° C
- temperatureThe reaction solution was cooled to room temperature
- extractionextracted with ethyl acetate
- washThe organic layer was washed with dilute hydrochloric acid and saturated saline
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a39218ba7aa246a0a5ee7335efd3b5d7
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06537948B1
Reaction notes
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