Acetone → 1-(4-Acetylphenoxy)methyl-5-chloropyrimidin-2-one
Reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11]Cl)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].Cl.[Cl:14][C:15]1[CH:16]=[N:17][C:18](=[O:21])[NH:19][CH:20]=1.C(N(CC)CC)C.CC(C)=O>ClCCl>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][N:19]2[CH:20]=[C:15]([Cl:14])[CH:16]=[N:17][C:18]2=[O:21])=[CH:8][CH:9]=1)(=[O:3])[CH3:2]Participants
6
Procedure
The title compound was prepared in a manner similar to that described in Example 6 by adding a solution of 4-acetyl-1-(chloromethoxy)benzene [see Preparation 7] (2.2 mmol) in dichloromethane (5 ml) to a solution of 5-chloropyrimidin-2-one hydrochloride (2.2 mmol) and triethylamine (4.4 mmol) in dichloromethane (20 ml). The product was the desired N-alkylated isomer; yield: 0.60 g (100%), m.p. 182° C. (acetone). (Found C56.38 H4.15 Calc. for C13H11ClN2O3 : C56.02; H3.99) 1H NMR (CDCl3): δ 2.50 (Me), 5.82 (CH2), 7.0 and 7.8 (H-4 and H-6, respectively, J 3 Hz). [70 eV, m/z, % rel. int.)]: 278 (7,M), 145 (31), 143 (100), 136 (18), 121 (33), 116 (22), 93 (15).
Sources & evidence
- ORD record
- ord-43beb57e7ff74cac896308d2f4b6ba37
- Source dataset
- uspto-grants-1987_11
- Patent number
- US04705791
Reaction notes
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