Triethylamine → 2(1H)-Pyrimidinone, 5-chloro-1-[(phenylmethoxy)methyl]-
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.[CH2:17]([O:24][CH2:25]Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>ClCCl>[CH2:17]([O:24][CH2:25][N:5]1[CH:4]=[C:3]([Cl:2])[CH:8]=[N:7][C:6]1=[O:9])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Participants
Procedure
A mixture of 5-chloropyrimidin-2-one hydrochloride (10 mmol) and triethylamine (20 mmol) in dichloromethane (50 ml) were stirred together until all the solid material had dissolved, before a solution of chloromethyl benzyl ether (see Preparation 1a and 1b) (10 mmol) in dichloromethane (10 ml) was added with stirring at room temperature. The mixture was stirred for 3 hours at room temperature before the solvent was distilled off. The residue was triturated with water (40 ml), extracted into chloroform (3×40 ml) and the dried (MgSO4) solution evaporated; yield 2.40 g (96%). The product was purified by trituration with ether and had m.p. 125° C. (acetone). 1H NMR (CDCl3): δ4.68 (CH2Ph), 5.32 (CH2O), 7.30 (Ph), 7.72 and 8.48 (H-4, H-6, J 3 Hz).
Workup
- additionwas added
- stirringwith stirring at room temperature
- stirringThe mixture was stirred for 3 hours at room temperature before the solvent
- distillationwas distilled off
- customThe residue was triturated with water (40 ml)
- extractionextracted into chloroform (3×40 ml)
- dry with materialthe dried (MgSO4) solution
- customevaporated
- customThe product was purified by trituration with ether
Sources & evidence
- ORD record
- ord-ad128ffbe21d48b18a9d49b215b89ebf
- Source dataset
- uspto-grants-1985_09
- Patent number
- US04539324
Reaction notes
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