Triphenylphosphine → 1,3-dimethyl-6-(4-[2-(2-phenyl-4-oxo-4H-1-benzopyran-6-yl)oxyethyl]piperazine-1-yl)-2,4(1H,3H)-pyrimidinedione

HRID 1196724Notes

Reaction equation

HRID 1196724 reaction equation
[CH3:1][N:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]2)=[CH:6][C:5](=[O:17])[N:4]([CH3:18])[C:3]1=[O:19].O[C:21]1[CH:22]=[CH:23][C:24]2[O:29][C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:27][C:26](=[O:36])[C:25]=2[CH:37]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C([O-])(=O)C([O-])=O>O1CCCC1>[CH3:1][N:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:21]3[CH:22]=[CH:23][C:24]4[O:29][C:28]([C:30]5[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=5)=[CH:27][C:26](=[O:36])[C:25]=4[CH:37]=3)[CH2:10][CH2:9]2)=[CH:6][C:5](=[O:17])[N:4]([CH3:18])[C:3]1=[O:19]

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 71081OxalateHCID 722796-Hydroxyflavone2×HCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 99702521,3-dimethyl-6-[4-(2-hydroxyethyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione2×

Product 1

HCID 198987561,3-dimethyl-6-(4-[2-(2-phenyl-4-oxo-4H-1-benzopyran-6-yl)oxyethyl]piperazine-1-yl)-2,4(1H,3H)-pyrimidinedioneYield 61.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The same procedure as in Example 8-(2) was effected so as to react and treat 0.8 g of 1,3-dimethyl-6-[4-(2-hydroxyethyl)piperazine-1-yl]-2,4(1H,3H)-pyrimidinedione (Compound 30), 1.19 g of 6-hydroxy-2-phenyl-4-oxo-4H-1-benzopyran (Compound 27), 40 ml of tetrahydrofuran containing 1.05 g of triphenylphosphine and 0.63 ml of diethyl azodicarboxylate, in order to obtain 0.89 g (yield 58%) of 1,3-dimethyl-6-(4-[2-(2-phenyl-4-oxo-4H-1-benzopyran-6-yl)oxyethyl]piperazine-1-yl)-2,4(1H,3H)-pyrimidinedione (the non-oxalate, of Compound 31).

Workup

  1. customto react

Sources & evidence

ORD record
ord-e8776004f3fa429aa0b2871a6cb4d43c
Source dataset
uspto-grants-1992_05
Patent number
US05114941

Reaction notes

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