Ammonium formate → 3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-5-methyl-2,4(1H,3H)-pyrimidinedione

HRID 342605Notes

Reaction equation

HRID 342605 reaction equation
C([N:8]1[CH:13]=[C:12]([CH3:14])[C:11](=[O:15])[N:10]([CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[O:31][CH3:32])[CH2:21][CH2:20]2)[C:9]1=[O:33])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd]>[CH3:32][O:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[N:22]1[CH2:21][CH2:20][N:19]([CH2:18][CH2:17][CH2:16][N:10]2[C:11](=[O:15])[C:12]([CH3:14])=[CH:13][NH:8][C:9]2=[O:33])[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 10874021HCID 10874021, compound

Product 1

HCID 158406623-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-5-methyl-2,4(1H,3H)-pyrimidinedioneYield 71.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 1-benzyl-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-5-methyl-2,4(1H,3H)-pyrimidinedione (809 mg, 1.8 mmol), prepared as in Example 25, 10% palladium on carbon (800 mg) and of 0.1N ammonium formate (180 mL, 18 mmol in methanol) was heated 10 hours at reflux. The reaction mixture then was filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (30 g) eluting with ethyl acetate to give 3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-5-methyl-2,4(1H,3H)-pyrimidinedione (459 mg, 1.28 mmol), m.p. 168°-170° C. The free base was recrystallized from a solution of hydrochloric acid in methanol to give 3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-5-methyl-2,4(1H,3H)-pyrimidinedione hydrochloride, m.p. 245°-248° C. Anal.: Calcd. for C19H26N4O3.(HCl)2 : C, 50.99; H, 6.71; N, 12.52%; Found: C, 51.06; H, 6.47; N, 12.58%.

Workup

  1. temperatureat reflux
  2. filtrationThe reaction mixture then was filtered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel (30 g)
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-0126d9d4be3b4e1e903d331efbdcd65c
Source dataset
uspto-grants-1999_01
Patent number
US05859014

Reaction notes

Loading…