3-(4-Ethoxyphenyl)prop-2-enoic acid → 1H-Purine-2,6-dione, 3,7-dihydro-1,3-dipropyl-8-(2-(4-ethoxyphenyl)ethenyl)-, (E)-

HRID 375330Notes

Reaction equation

HRID 375330 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]([O:19][C:20]1[CH:30]=[CH:29][C:23]([CH:24]=[CH:25][C:26](O)=O)=[CH:22][CH:21]=1)[CH3:18]>>[CH2:17]([O:19][C:20]1[CH:30]=[CH:29][C:23](/[CH:24]=[CH:25]/[C:26]2[NH:1][C:2]3[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]=3[N:8]=2)=[CH:22][CH:21]=1)[CH3:18]

Participants

3

Reactant 2

HCID 2955753-(4-Ethoxyphenyl)prop-2-enoic acidHCID 50986055,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 64487951H-Purine-2,6-dione, 3,7-dihydro-1,3-dipropyl-8-(2-(4-ethoxyphenyl)ethenyl)-, (E)-Yield 70.2%

Procedure

Substantially the same procedure as in Reference Example 1 was repeated using 3.0 g (13.3 mmol) of 5,6-diamino-1,3-dipropyluracil and 2.80 g (14.6 mmol) of 4-ethoxycinnamic acid. Then, the resultant crude crystals were recrystallized from dioxane to give 3.57 g (yield 70%) of Compound 47 as pale yellow needles.

Workup

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

Sources & evidence

ORD record
ord-8ff2038c9cc7448fa677d3ae10bcd309
Source dataset
uspto-grants-1996_01
Patent number
US05484920

Reaction notes

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