HCID 12343563, compound → 5-Chloro-1-(1-phenoxyethyl)pyrimidin-2(1H)-one

HRID 247072Notes

Reaction equation

HRID 247072 reaction equation
Cl[CH:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:3].Cl.[Cl:12][C:13]1[CH:14]=[N:15][C:16](=[O:19])[NH:17][CH:18]=1>ClCCl>[O:4]([CH:2]([N:17]1[CH:18]=[C:13]([Cl:12])[CH:14]=[N:15][C:16]1=[O:19])[CH3:3])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 12343563HCID 12343563, compoundHCID 126485235-Chloropyrimidin-2-ol hydrochloride

Product 1

HCID 130629405-Chloro-1-(1-phenoxyethyl)pyrimidin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The title compound was prepared in a manner similar to that described in Example 6 by adding a solution of α-chloroethoxybenzene [see Preparation 8] (4.5 mmol) in dichloromethane (5 ml) to a solution from 5-chloropyrimidin-2-one hydrochloride (4.5 mmol) in dichloromethane (15 ml) at 5° C., and the mixture was stirred at room temperature for 2 h before being worked up. The product was a mixture of the desired N-isomer and the O-isomer in the ratio 3:2; yield 0.85 g (76%). The isomers were separated by chromatography on silica gel using chloroform as above; m.p. 92° C. (CH2Cl2 /Pet.ether). (Found: C58.02; H 4.51 Calc. for C12H11ClN2O2 : C57.49; H4.43) 1H NMR (CDCl3): δ 1.72 (Me, d, J 5Hz), 6.4-7.3 (Ph,H-α), 7.79 and 8.40 (H-4 and H-6, respectively, J 3 Hz). IR (KBr): 1665 cm-1 (CO). MS [70 eV, m/z (% rel. int.)]: 250 (l,M), 159 (30)), 157 (100), 121 (23), 77 (30), 65 (17).

Workup

  1. additiona mixture of the desired N-isomer
  2. customThe isomers were separated by chromatography on silica gel

Sources & evidence

ORD record
ord-34ae26041af24e92adf6fc28f977f63f
Source dataset
uspto-grants-1987_11
Patent number
US04705791

Reaction notes

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