3-(1,3-Benzodioxol-5-yl)prop-2-enoic acid → 1H-Purine-2,6-dione, 3,7-dihydro-8-(2-(1,3-benzodioxol-5-yl)ethenyl)-1,3-dipropyl-, (E)-, hydrate

HRID 375290

Reaction equation

HRID 375290 reaction equation
[NH2:1][C:2]1[C:3](=[O:16])[N:4]([CH2:13][CH2:14][CH3:15])[C:5](=[O:12])[N:6]([CH2:9][CH2:10][CH3:11])[C:7]=1[NH2:8].[CH2:17]1[O:30][C:29]2[CH:28]=[CH:27][C:21]([CH:22]=[CH:23][C:24](O)=O)=[CH:20][C:19]=2[O:18]1>>[CH2:17]1[O:30][C:29]2[CH:28]=[CH:27][C:21](/[CH:22]=[CH:23]/[C:24]3[NH:1][C:2]4[C:3](=[O:16])[N:4]([CH2:13][CH2:14][CH3:15])[C:5](=[O:12])[N:6]([CH2:9][CH2:10][CH3:11])[C:7]=4[N:8]=3)=[CH:20][C:19]=2[O:18]1

Participants

3

Reactant 2

HCID 169173-(1,3-Benzodioxol-5-yl)prop-2-enoic acidHCID 50986055,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 64488101H-Purine-2,6-dione, 3,7-dihydro-8-(2-(1,3-benzodioxol-5-yl)ethenyl)-1,3-dipropyl-, (E)-, hydrateYield 69%

Procedure

Substantially the same procedure as in Reference Example 1 was repeated using 4.25 g (18.8 mmol) of 5,6-diamino-1,3-dipropyluracil and 4.33 g (22.6 mmol) of 3,4-methylenedioxycinnamic acid. Then, the resultant crude crystals were recrystallized from dioxane to give 4.92 g (yield 69%) of Compound 18 as a pale yellow powder.

Workup

  1. customThen, the resultant crude crystals were recrystallized from dioxane

Sources & evidence

ORD record
ord-ad71b5ae2dd04baea6a019bb01f1f6d0
Source dataset
uspto-grants-1996_01
Patent number
US05484920

Linked notes

Loading…