5-Chloropyrimidin-2-ol hydrochloride → 1-(3-Trifluoromethylphenoxy)methyl-5-chloropyrimidin-2-one
Reaction equation
Cl[CH2:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1.Cl.[Cl:15][C:16]1[CH:17]=[N:18][C:19](=[O:22])[NH:20][CH:21]=1>ClCCl>[F:11][C:10]([F:13])([F:12])[C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[O:3][CH2:2][N:20]1[CH:21]=[C:16]([Cl:15])[CH:17]=[N:18][C:19]1=[O:22]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1-chloromethoxy-3-trifluoromethylbenzene [see Preparation 4) (7 mmol) in dichloromethane (10 ml) was added to a solution of 5-chloropyrimidin-2-one hydrochloride (70 mmol) in dichloromethane (30 ml) and the mixture stirred at room temperature for 18 h. The solvent was then distilled off, the mixture triturated with water, the residual solid extracted with chloroform and the dried (MgSO4) chloroform solution evaporated; yield 1.88 g (94%). The product was a mixture of the N- and O-isomer in the ratio 3:1. The isomers were separated by the difference in their solutilities in tetrachloromethane, the O-isomer being the more solunble. The title compound, the N-isomer was isolated in a non-crystalline form. 1H NMR (CDCl3) δ 5.82 (CH2), 7.1-7.3 (Ph), 7.85 (H-4, J4,6 3 Hz), 8.45 (H-6).
Workup
- distillationThe solvent was then distilled off
- customthe mixture triturated with water
- extractionthe residual solid extracted with chloroform
- dry with materialthe dried (MgSO4) chloroform solution
- customevaporated
- additiona mixture of the N-
- customThe isomers were separated by the difference in their solutilities in tetrachloromethane
Sources & evidence
- ORD record
- ord-73bcde404abf44a5b99a87f2a87d64a9
- Source dataset
- uspto-grants-1986_06
- Patent number
- US04596870
Reaction notes
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