Triphenylphosphine → 1,3-dimethyl-6-[4-(3-[2-methoxy-4-nitrophenyloxy]propyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione

HRID 1729285Notes

Reaction equation

HRID 1729285 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[OH:12].[CH3:13][N:14]1[C:19]([N:20]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28]O)[CH2:22][CH2:21]2)=[CH:18][C:17](=[O:30])[N:16]([CH3:31])[C:15]1=[O:32].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:13][N:14]1[C:19]([N:20]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][O:12][C:4]3[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=3[O:2][CH3:1])[CH2:22][CH2:21]2)=[CH:18][C:17](=[O:30])[N:16]([CH3:31])[C:15]1=[O:32]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 767382-Methoxy-4-nitrophenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 103564171,3-dimethyl-6-[4-(3-hydroxypropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 190120801,3-dimethyl-6-[4-(3-[2-methoxy-4-nitrophenyloxy]propyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedioneYield 87.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 20 ml of anhydrous tetrahydrofuran were suspended 0.68 g of 2-methoxy-4-nitrophenol, 1.0 g of 1,3-dimethyl-6-[4-(3 -hydroxypropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione (Compound a) and 1.1 g of triphenylphosphine, and 0.71 ml of diethyl azodicarboxylate was added to the resultant suspension. Afterward, the mixture was treated in the same manner as in Reference Example 4, followed by recrystallizing from methanol to obtain 1.35 g of oily 1,3-dimethyl-6-[4-(3-[2-methoxy-4-nitrophenyloxy]propyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione (Compound w).

Workup

  1. additionAfterward, the mixture was treated in the same manner as in Reference Example 4
  2. customby recrystallizing from methanol

Sources & evidence

ORD record
ord-496534f5c40047ae9486cab1340b2c24
Source dataset
uspto-grants-1994_07
Patent number
US05332739

Reaction notes

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