1-benzyl-3-(3-chloropropyl)-5-methyl-2,4(1H,3H)-pyrimidinedione → 3-(3-chloropropyl)-5-methyl-2,4(1H,3H)-pyrimidinedione

HRID 342555Notes

Reaction equation

C([N:8]1[CH:13]=[C:12]([CH3:14])[C:11](=[O:15])[N:10]([CH2:16][CH2:17][CH2:18][Cl:19])[C:9]1=[O:20])C1C=CC=CC=1>[Pd].C([O-])=O.[NH4+].CO>[Cl:19][CH2:18][CH2:17][CH2:16][N:10]1[C:11](=[O:15])[C:12]([CH3:14])=[CH:13][NH:8][C:9]1=[O:20]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 1-benzyl-3-(3-chloropropyl)-5-methyl-2,4(1H,3H)-pyrimidinedione (1 g, 3.41 mmol), prepared as in Example 19, 10% palladium on carbon (1 g) and 0.1M ammonium formate/methanol (340 mL) was heated 3 hours at reflux under argon. The reaction mixture was allowed to cool to 25° C., then filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane-ethyl acetate (1:1) to give 3-(3-chloropropyl)-5-methyl-2,4(1H,3H)-pyrimidinedione (0.52 g, 2.57 mmol), m.p. 117°-121° C.

Workup

temperaturewas heated 3 hours
temperatureat reflux under argon
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography on silica gel eluting with hexane-ethyl acetate (1:1)

Sources & evidence

ORD record: ord-97df699b140b4ed1bcd97f5f7a02ca66
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05859014

Reaction notes

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