Triphenylphosphine → HCID 20061205, compound

HRID 1085274Notes

Reaction equation

HRID 1085274 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[CH3:12][N:13]1[C:18]([NH:19][CH2:20][CH2:21][NH:22][C:23](=O)[C:24]2[CH:29]=CC([N+]([O-])=O)=CC=2)=[CH:17][C:16](=[O:34])[N:15]([CH3:35])[C:14]1=[O:36].[C:37]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:38]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:12][N:13]1[C:18]([N:19]2[CH2:20][CH2:21][N:22]([CH2:23][CH2:24][CH2:29][O:11][C:3]3[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=3[NH2:1])[CH2:38][CH2:37]2)=[CH:17][C:16](=[O:34])[N:15]([CH3:35])[C:14]1=[O:36]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 36133892-Amino-4-NitrophenolHCID 20061251HCID 20061251, compound2×

Product 1

HCID 20061205HCID 20061205, compoundYield 17.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.54 g of 2-amino-4-nitrophenol, 2.82 g of 1,3-dimethyl-6-[4-(3-hydroxypropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione (Compound 139) and 2.88 g of triphenylphosphine were suspended in 20 ml of anhydrous tetrahydrofuran, followed by the addition of 1.92 g of diethyl azodicarboxylate. The thus-prepared mixture was stirred for 1 hour at room temperature and a precipitate was collected by filtration. The precipitate was washed with chloroform-ether to obtain 1.44 g of crytals. The crystals were recrystallized from ethanol-chloroform, thereby obtaining 0.6 g of 1,3-dimethyl-6-{4-[3-(2-amino-4-nitrophenyloxy)propyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione as crystals.

Workup

  1. filtrationa precipitate was collected by filtration
  2. washThe precipitate was washed with chloroform-ether
  3. customto obtain 1.44 g of crytals
  4. customThe crystals were recrystallized from ethanol-chloroform

Sources & evidence

ORD record
ord-08d6a630c385468e8f7b66abc3f3284e
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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