Carbon Dioxide → 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid
Reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[N:17]=[C:16]([S:21][CH3:22])[N:15]=1.[C:23](=[O:25])=[O:24].Cl>O1CCCC1.CCCCCC.O>[Cl:13][C:14]1[C:19]([C:23]([OH:25])=[O:24])=[C:18]([Cl:20])[N:17]=[C:16]([S:21][CH3:22])[N:15]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of diisopropylamine 11.93 g in tetrahydrofuran 350 ml is dropped a 1.6M solution of n-butyl lithium in hexane 73.7 ml over a period of 20 minutes on dry ice-acetone bath, and the mixture is stirred for 30 minutes. Thereto is added 4,6-dichloro-2-methylthiopyrimidine 10.00 g in tetrahydrofuran 50 ml over a period of 1 hour on a dry ice-acetone bath, followed by further one hour agitation. The reaction mixture is poured into dry ice and the mixture is stirred for 1.5 hours at room temperature. The reaction mixture is made acidic with 10% hydrochloric acid, diluted with water and extracted with ethyl acetate. The organic layer is washed, dried and condensed in vacuo. The resulting solid is triturated with hexane to give 4,6-dichloro-5-carboxy-2-methylthiopyrimidine as a brown crystalline powder, 10.42 g. mp 151–158° C.(decomposition)
Workup
- waitfollowed by further one hour
- stirringthe mixture is stirred for 1.5 hours at room temperature
- extractionextracted with ethyl acetate
- washThe organic layer is washed
- customdried
- customcondensed in vacuo
- customThe resulting solid is triturated with hexane
Sources & evidence
- ORD record
- ord-4d883bf271244e7a911872ebcf12aca4
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07220736B2
Reaction notes
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