Fluorocinnamic acid → 1,3-diethyl-8-[(E)-1-fluoro-2-phenylethenyl]-7H-purine-2,6-dione

HRID 375351Notes

Reaction equation

HRID 375351 reaction equation
[NH2:1][C:2]1[C:3](=[O:14])[N:4]([CH2:12][CH3:13])[C:5](=[O:11])[N:6]([CH2:9][CH3:10])[C:7]=1[NH2:8].[F:15][C:16](=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:17](O)=O>>[CH2:12]([N:4]1[C:3](=[O:14])[C:2]2[NH:1][C:17](/[C:16](/[F:15])=[CH:20]\[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:8][C:7]=2[N:6]([CH2:9][CH3:10])[C:5]1=[O:11])[CH3:13]

Participants

3

Reactant 2

HCID 98321Fluorocinnamic acidHCID 45721335,6-Diamino-1,3-diethyluracil

Product 1

HCID 208411351,3-diethyl-8-[(E)-1-fluoro-2-phenylethenyl]-7H-purine-2,6-dioneYield 58%

Procedure

Substantially the same procedure as in Example 7 was repeated using 1.08 g (5.47 mmol) of 5,6-diamino-1,3-diethyluracil and 1.00 g (6.02 mmol) of α-fluorocinnamic acid. Then, the resultant crude crystals were recrystallized from dioxane/water to give 1.04 g (yield 58%) of Compound 138 as white plates.

Workup

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

Sources & evidence

ORD record
ord-3d940c0c6e9540ceb3556a9ffc0a314f
Source dataset
uspto-grants-1996_01
Patent number
US05484920

Reaction notes

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