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

HRID 1729284Notes

Reaction equation

HRID 1729284 reaction equation
[Cl: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]([N:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27]O)[CH2:21][CH2:20]2)=[CH:17][C:16](=[O:29])[N:15]([CH3:30])[C:14]1=[O:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:12][N:13]1[C:18]([N:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][O:11][C:3]3[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=3[Cl:1])[CH2:21][CH2:20]2)=[CH:17][C:16](=[O:29])[N:15]([CH3:30])[C:14]1=[O:31]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 12074NitrofunginHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 103564171,3-dimethyl-6-[4-(3-hydroxypropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 190118781,3-dimethyl-6-[4-(3-[2-chloro-4-nitrophenyloxy]propyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedioneYield 47.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 70 ml of anhydrous tetrahydrofuran were suspended 2.4 g of 2-chloro-4-nitrophenol, 3.38 g of 1,3-dimethyl-6-[4-(3-hydroxypropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione (Compound a) and 3.62 g of triphenylphosphine, and 2.4 g of diethyl azodicarboxylate was added to the resultant suspension. Afterward, the resultant mixture was treated in the same manner as in Reference Example 4 to obtain 2.5 g of light yellow crystals. The crystals were recrystallized from ethanol to obtain 2.07 g of crystalline 1,3-dimethyl-6-[4-(3-[2-chloro-4-nitrophenyloxy]propyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione (Compound u).

Sources & evidence

ORD record
ord-d7607782196347eba4b5eb2d25b404e2
Source dataset
uspto-grants-1994_07
Patent number
US05332739

Reaction notes

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