Triethylamine → 2-[(4-methylpyridin-2-yl)methyl]thio-6-methyl-4(3H)-pyrimidinone
Reaction equation
O[CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][N:4]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[CH3:22][C:23]1[NH:28][C:27](=[S:29])[NH:26][C:25](=[O:30])[CH:24]=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[OH-].[Na+].C(Cl)(Cl)Cl>[CH3:9][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([CH2:2][S:29][C:27]2[NH:26][C:25](=[O:30])[CH:24]=[C:23]([CH3:22])[N:28]=2)[CH:8]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
A mixture containing 1.23 g (10 mmol) of 2-hydroxymethyl-4-methylpyridine [Bull. Chem. Soc. Jap. 3, 413 (1955)], 2.1 ml (15 mmol) of triethylamine and 25 ml of chloroform is cooled to 0° C. and 0.85 ml (11.7 mmol) of methanesulfonyl chloride is added under stirring. After stirring for 30 minutes 0.2 g of benzyltriethylammonium chloride and 1.42 g (10 mmol) of 6-methyl-2-thiouracil dissolved in 20 ml of 1N sodium hydroxide solution are added, then the reaction mixture is vigorously stirred at room temperature for 10 hours and worked up in the usual manner. The crude product obtained is crystallized by thoroughly triturating it with diisopropyl ether, m.p.: 157°-158° C. The product obtained is further purified by recrystallization from the mixture of toluene and ethyl acetate to obtain 1.19 g (48%) of the title compound, m.p.: 161°-162° C.
Workup
- additionare added
- stirringthe reaction mixture is vigorously stirred at room temperature for 10 hours
- customThe crude product obtained
- customis crystallized
- customby thoroughly triturating it with diisopropyl ether, m.p.: 157°-158° C
- customThe product obtained
- customis further purified by recrystallization from the mixture of toluene and ethyl acetate
Sources & evidence
- ORD record
- ord-1d02cb6435e7435f998313618a96f080
- Source dataset
- uspto-grants-1991_08
- Patent number
- US05037830
Reaction notes
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