3-Methylpyridine → 3-Trimethylacetyloxy-2-[1-(ethoxyimino)butyl]-5-(4,6-dimethoxy-2-methylthio-5-pyrimidyl)cyclohex-2-en-1-one
Reaction equation
N1C=CC=C(C)C=1.[CH2:8]([O:10][N:11]=[C:12]([C:16]1[C:17](=[O:35])[CH2:18][CH:19]([C:23]2[C:24]([O:33][CH3:34])=[N:25][C:26]([S:31][CH3:32])=[N:27][C:28]=2[O:29][CH3:30])[CH2:20][C:21]=1[OH:22])[CH2:13][CH2:14][CH3:15])[CH3:9].[CH3:36][C:37]([CH3:42])([CH3:41])[C:38](Cl)=[O:39]>ClCCl>[CH3:36][C:37]([CH3:42])([CH3:41])[C:38]([O:22][C:21]1[CH2:20][CH:19]([C:23]2[C:28]([O:29][CH3:30])=[N:27][C:26]([S:31][CH3:32])=[N:25][C:24]=2[O:33][CH3:34])[CH2:18][C:17](=[O:35])[C:16]=1[C:12](=[N:11][O:10][CH2:8][CH3:9])[CH2:13][CH2:14][CH3:15])=[O:39]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3-picoline (40 mg) and 2-[1-ethoxyimino)butyl]-5-(4,6-dimethoxy-2-methylthio-5-pyrimidyl)cyclohex-2-en-1-one (2) (80 mg) in dichloromethane (10 ml) was treated with trimethylacetyl chloride with stirring at room temperature. After 2 hours the solution was washed with dilute hydrochloric acid (1M, 20 ml), separated, dried over anhydrous magnesium sulphate and evaporated under reduced pressure to give 3-trimethylacetyloxy-2-[1-(ethoxyimino)butyl]-5-(4,6-dimethoxy-2-methylthio-5-pyrimidyl)cyclohex-2-en-1-one (7) as a pale brown oil (100 mg) which was characterized by nuclear magnetic resonance spectroscopy.
Workup
- washAfter 2 hours the solution was washed with dilute hydrochloric acid (1M, 20 ml)
- customseparated
- dry with materialdried over anhydrous magnesium sulphate
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-4ab3fa472c424ddf8655405e0f98390d
- Source dataset
- uspto-grants-1987_04
- Patent number
- US04659362
Reaction notes
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