Triethylamine → 5-Chloro-1-{[(naphthalen-2-yl)oxy]methyl}pyrimidin-2(1H)-one
Reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[N:5][C:6](=[O:9])[NH:7][CH:8]=1.C(N(CC)CC)C.Cl[CH2:18][O:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1>C(Cl)Cl>[CH:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[CH:29][C:20]=1[O:19][CH2:18][N:5]1[CH:4]=[C:3]([Cl:2])[CH:8]=[N:7][C:6]1=[O:9]Participants
Procedure
5-Chloropyrimidine-2-one hydrochloride (5 mmol) and triethylamine were stirred together in CH2Cl2 (30 ml). When all the solid had dissolved there was added a solution of 2-chloromethoxynaphthalene [see Preparation 13] (5 mmol) in CH2Cl2 (10 ml) with stirring at room temperature for 5 minutes. The mixture was stirred at room temperature for 24 hours before the solvent was distilled off. The residue was triturated with water, extracted into CHCl3, dried (MgSO4) and evaporated to give a mixture of the title compound and the O-alkylated isomer in the ratio 4:1. Yield 1.27g (86%). The O-isomer was removed from the product by extraction with ether followed by recrystallization of the N-isomer from acetone m.p. 168° C. 1H NMR (CDCl3 δ): 5.85 (s, CH2), 7.10-8.1 (m, 8H. Ar+ H-4), 8.48 (H-6, d7 =4Hz) IR (KBr, cm -1): 1675 (CO).
Workup
- dissolutionWhen all the solid had dissolved there
- stirringThe mixture was stirred at room temperature for 24 hours before the solvent
- distillationwas distilled off
- customThe residue was triturated with water
- extractionextracted into CHCl3
- dry with materialdried (MgSO4)
- customevaporated
- customto give
Sources & evidence
- ORD record
- ord-9cae7ae3fb0c43e7a9d0db11d9e2fc65
- Source dataset
- uspto-grants-1987_11
- Patent number
- US04705791
Reaction notes
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