5-Amino-1-cyclohexyl-5-ethylbarbituric acid → 1-Cyclohexyl-5-ethyl-5-(4,5,6,7-tetrafluoro-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-2,4,6(1H,3H,5H)-pyrimidinetrione

HRID 1097277

Reaction equation

HRID 1097277 reaction equation
[NH2:1][C:2]1([CH2:17][CH3:18])[C:7](=[O:8])[N:6]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:5](=[O:15])[NH:4][C:3]1=[O:16].C(N1C(=O)C(C)(N2[C:36](=[O:37])[C:35]3[C:30](=[C:31]([F:41])[C:32]([F:40])=[C:33]([F:39])[C:34]=3[F:38])[C:29]2=[O:42])C(=O)NC1=O)C>>[CH:9]1([N:6]2[C:7](=[O:8])[C:2]([CH2:17][CH3:18])([N:1]3[C:29](=[O:42])[C:30]4[C:35](=[C:34]([F:38])[C:33]([F:39])=[C:32]([F:40])[C:31]=4[F:41])[C:36]3=[O:37])[C:3](=[O:16])[NH:4][C:5]2=[O:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 154249365-Amino-1-cyclohexyl-5-ethylbarbituric acidHCID 247656681-Ethyl-5-methyl-5-(4,5,6,7-tetrafluoro-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-2,4,6(1H,3H,5H)-pyrimidinetrione

Product 1

HCID 247656691-Cyclohexyl-5-ethyl-5-(4,5,6,7-tetrafluoro-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-2,4,6(1H,3H,5H)-pyrimidinetrione

Procedure

Compound 19i was prepared from 5-amino-1-cyclohexyl-5-ethylbarbituric acid (0.38 g, 1.50 mmol) using the same procedure described for 19f. The crude product was recrystallized from EtOH to give 1-cyclohexyl-5-ethyl-5-(tetrafluorophthalimido)barbituric acid (19i) as white crystals.

Workup

  1. customThe crude product was recrystallized from EtOH

Sources & evidence

ORD record
ord-de55129afb3543618c7987d87d1d81a1
Source dataset
uspto-grants-2012_03
Patent number
US08143252B2

Linked notes

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