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

HRID 1196723Notes

Reaction equation

HRID 1196723 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:8][C:7](=[O:17])[C:6]=2[CH:18]=1.[CH3:19][N:20]1[C:25]([N:26]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][CH2:34]O)[CH2:28][CH2:27]2)=[CH:24][C:23](=[O:36])[N:22]([CH3:37])[C:21]1=[O:38].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.C(O)(=O)C(O)=O.CN1C(N2CCN(CCCOC3C=CC4OC(C5C=CC=CC=5)=CC(=O)C=4C=3)CC2)=CC(=O)N(C)C1=O>O1CCCC1>[CH3:19][N:20]1[C:25]([N:26]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][CH2:34][O:1][C:2]3[CH:3]=[CH:4][C:5]4[O:10][C:9]([C:11]5[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=5)=[CH:8][C:7](=[O:17])[C:6]=4[CH:18]=3)[CH2:28][CH2:27]2)=[CH:24][C:23](=[O:36])[N:22]([CH3:37])[C:21]1=[O:38]

Participants

8

Reactant 6

HCID 11776TriphenylphosphineHCID 71081OxalateHCID 722796-Hydroxyflavone2×HCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 103564171,3-dimethyl-6-[4-(3-hydroxypropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione2×HCID 198987901,3-dimethyl-6-(4-[3-(2-phenyl-4-oxo-4H-1-benzopyran-6-yl)oxypropyl]piperazine-1-yl)-2,4(1H,3H)-pyrimidinedione oxalate

Product 1

HCID 198987631,3-dimethyl-6-(4-[3-(2-phenyl-4-oxo-4H-1-benzopyran-6-yl)oxypropyl]piperazine-1-yl)-2,4(1H,3H)-pyrimidinedioneYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 40 ml of tetrahydrofuran were dissolved 0.84 g of 6-hydroxy-2-phenyl-4-oxo-4H-1-benzopyran (Compound 27), 0.5 g of the previously obtained 1,3-dimethyl-6-[4-(3-hydroxypropyl)piperazine-1-yl]-2,4(1H,3H)-pyrimidinedione (Compound 26) and 0.66 g of triphenylphosphine. Then, 0.4 ml of diethyl azodicarboxylate was added to the solution, followed by stirring for 1 hour. The resultant reaction solution was concentrated under reduced pressure, and the resultant residue was purified through a silica gel column chromatograph (chloroform:methanol=40:1 in volume ratio) to obtain 0.41 g (yield 43%) of 1,3-dimethyl-6-(4-[3-(2-phenyl-4-oxo-4H-1-benzopyran-6-yl)oxypropyl]piperazine-1-yl)-2,4(1H,3H)-pyrimidinedione (the non-oxalate of Compound 28).

Workup

  1. customThe resultant reaction solution
  2. concentrationwas concentrated under reduced pressure
  3. customthe resultant residue was purified through a silica gel column chromatograph (chloroform:methanol=40:1 in volume ratio)

Sources & evidence

ORD record
ord-bddc6a10936d4388997589a4cd64b59b
Source dataset
uspto-grants-1992_05
Patent number
US05114941

Reaction notes

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