3-(3-chloropropyl)-5-methyl-2,4(1H,3H)-pyrimidinedione → HCID 15840648, compound

HRID 342560Notes

Reaction equation

HRID 342560 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:10](=[O:11])[C:9]([CH3:12])=[CH:8][NH:7][C:6]1=[O:13].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[C:17]([O:27][CH3:28])[CH:16]=1>>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:22][CH2:23][N:24]([CH2:2][CH2:3][CH2:4][N:5]3[C:10](=[O:11])[C:9]([CH3:12])=[CH:8][NH:7][C:6]3=[O:13])[CH2:25][CH2:26]2)=[C:17]([O:27][CH3:28])[CH:16]=1

Participants

3

Reactant 2

HCID 110418353-(3-chloropropyl)-5-methyl-2,4(1H,3H)-pyrimidinedioneHCID 158406631-(4-Chloro-2-methoxyphenyl)piperazine

Product 1

HCID 15840648HCID 15840648, compound

Conditions

Temperature
25 °C

Procedure

A mixture of 3-(3-chloropropyl)-5-methyl-2,4(1H,3H)-pyrimidinedione (223 mg, 0.98 mmol), prepared as in Example 19, and 1-(4-chloro-2-methoxyphenyl)piperazine (200 mg, 0.98 mmol), prepared as in Example 12, was heated 2 hours with stirring at 180° to 190° C., allowed to cool to 25° C. and then purified by preparative thin layer chromatography on silica gel eluting with methylene chloride/(methylene chloride/methanol/ammonium hydroxide-60:10:1) (7:3) to give 3-{3-[4-(4-chloro-2-methoxyphenyl)piperazin-1-yl]propyl}-5-methyl-2,4(1H,3H)-pyrimidinedione. The free base was recrystallized from a solution of hydrogen chloride in methanol to give 3-{3-[4-(4-chloro-2-methoxyphenyl)piperazin-1-yl]propyl}-5-methyl-2,4(1H,3H)-pyrimidinedione hydrochloride, m.p. 182°-184° C. Anal.: Calcd. for C19H25ClN4O3.(HCl)2 : C, 48.25; H, 5.92; N, 11.84%; Found: C, 48.55; H, 5.81; N, 11.85%.

Workup

  1. temperaturewas heated 2 hours
  2. custompurified by preparative thin layer chromatography on silica gel eluting with methylene chloride/(methylene chloride/methanol/ammonium hydroxide-60:10:1) (7:3)

Sources & evidence

ORD record
ord-433b513c66cb4f8ba5e5a1d7c4ef214e
Source dataset
uspto-grants-1999_01
Patent number
US05859014

Reaction notes

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