tert-Butyl acetate → HCID 66955902, compound
Reaction equation
[OH:1][CH:2]([C:7]1[C:8]([CH3:26])=[N:9][C:10]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[N:11][C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)[C:3]([O:5][CH3:6])=[O:4].C(O[C:31]([CH3:34])([CH3:33])[CH3:32])(=O)C.Cl(O)(=O)(=O)=O>>[C:31]([O:1][CH:2]([C:7]1[C:8]([CH3:26])=[N:9][C:10]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[N:11][C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)[C:3]([O:5][CH3:6])=[O:4])([CH3:34])([CH3:33])[CH3:32]Participants
4
Procedure
To a solution of methyl 2-hydroxy-2-(4-methyl-2-(piperidin-1-yl)-6-p-tolylpyrimidin-5-yl)acetate (0.135 g; 0.380 mmol) in tert-butyl acetate (1.5 mL; 11.23 mmol) under nitrogen atmosphere was added perchloric acid 70% (0.049 mL; 0.570 mmol) and the reaction was stirred at room temperature for 2 days. The reaction was quenched by adding a saturated solution of sodium hydrogen carbonate. The mixture was extracted with ethyl acetate and the combined organic layers were dried over magnesium sulphate, filtered a,d concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (1-40%) in heptane furnished 0.063 g (40%) of the title compound as a colorless oil.
Workup
- customThe reaction was quenched
- additionby adding a saturated solution of sodium hydrogen carbonate
- extractionThe mixture was extracted with ethyl acetate
- dry with materialthe combined organic layers were dried over magnesium sulphate
- filtrationfiltered a,d
- concentrationconcentrated under reduced pressure
- customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (1-40%) in heptane
Sources & evidence
- ORD record
- ord-21abc7a0041d4b2b852fc787bf33e5cd
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08906906B2
Reaction notes
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