3-(Dimethylamino)acrylaldehyde → 2-methyl-N-(3-(pyrimidin-2-yl)oxetan-3-yl)propane-2-sulfinamide
Reaction equation
[CH3:1][C:2]([CH3:14])([S:4]([NH:6][C:7]1([C:11](=[NH:13])[NH2:12])[CH2:10][O:9][CH2:8]1)=[O:5])[CH3:3].CN(C)/[CH:17]=[CH:18]/[CH:19]=O.C[O-].[Na+]>CO.C(OCC)(=O)C>[CH3:3][C:2]([S:4]([NH:6][C:7]1([C:11]2[N:12]=[CH:19][CH:18]=[CH:17][N:13]=2)[CH2:10][O:9][CH2:8]1)=[O:5])([CH3:14])[CH3:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a yellow solution of 3-(1,1-dimethylethylsulfinamido)oxetane-3-carboximidamide (crude from above, assumed 0.494 mmol) in MeOH (2 ml) in a 50 ml sealed tube was added (E)-3-(dimethylamino)acrylaldehyde (0.090 g, 0.912 mmol), and the reaction mixture stirred for 10 min. Sodium methoxide (0.43 ml, 1.824 mmol, 25 wt % in MeOH) was added to the mixture, which was then stirred at 65° C. for overnight. The reaction mixture was diluted with ethyl acetate and washed with water. The aqueous layer was back extracted with ethyl acetate (3×25 ml). The combined organic layers was washed with saturated brine solution, dried over Na2SO4, filtered and concentrated. The crude material was purified by pre-HPLC. Overall yield of two steps: (30 mg, 24%).
Workup
- stirringwas then stirred at 65° C. for overnight
- washwashed with water
- extractionThe aqueous layer was back extracted with ethyl acetate (3×25 ml)
- washThe combined organic layers was washed with saturated brine solution
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude material was purified by pre-HPLC
Sources & evidence
- ORD record
- ord-ade5faed7d97427db8d7ad7715939420
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507683B2
Reaction notes
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