Triethylamine → 1-(2,4-Dichlorophenoxy)methyl-5-chloropyrimidin-2-one

HRID 1982556Notes

Reaction equation

Cl[CH2:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[Cl:11].[Cl:12][C:13]1[CH:14]=[N:15][C:16](=[O:19])[NH:17][CH:18]=1.C(N(CC)CC)C>ClCCl>[Cl:11][C:5]1[CH:6]=[C:7]([Cl:10])[CH:8]=[CH:9][C:4]=1[O:3][CH2:2][N:17]1[CH:18]=[C:13]([Cl:12])[CH:14]=[N:15][C:16]1=[O:19]

Participants

Conditions

Temperature: 40 °C

Procedure

The title compound was prepared in a manner similar to that described in Example 6 by the addition of a solution of 1-chloromethoxy-2,4-dichlorobenzene (see preparation 6) (5 mmol) in dichloromethane (25 ml) to a solution of 5-chloropyrimidin-2-one (5 mmol) and triethylamine (5 mmol) in dichloromethane (75 ml). The mixture was stirred at room temperature for 2 h and at 40° C. for 7 h before being worked up as above; yield 1.30 g (80%), isomer ratio 3:1. The title compound crystallized from DMSO: m.p. 170° C. 1H NMR (TFA): δ 6.10 (CH2),, 6.9-7.4 (Ph), 9.0-9.2 (H-4, H-6). IR (KBr): 1680 cm-1 (CO). MS (70 eV, m/z (% rel. int.)): 304 (l,M), 162 (3), 145 (35), 143 (100), 116 (28 ).

Workup

customThe title compound crystallized from DMSO

Sources & evidence

ORD record: ord-7f0441b6011345a9b43d92ff05b305dd
Source dataset: uspto-grants-1986_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04596870

Reaction notes

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