Triphenylphosphine → HCID 19011908, compound

HRID 1729287Notes

Reaction equation

HRID 1729287 reaction equation
[N+:1]([C:4]1(O)[CH:10]=[CH:9][CH:8]=[CH:7][CH:5]1O)([O-:3])=[O:2].[CH3:12][N:13]1[C:18]([N:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][OH:28])[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:54]>O1CCCC1>[CH3:12][N:13]1[C:18]([N:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][O:28][C:9]3[CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:7][C:8]=3[OH:54])[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 220568ethyl N-ethoxycarbonyliminocarbamateHCID 103564171,3-dimethyl-6-[4-(3-hydroxypropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedioneHCID 19011773HCID 19011773, compound

Product 1

HCID 19011908HCID 19011908, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 15 ml of anhydrous tetrahydrofuran were suspended 0.63 g of 2-nitrocatechol, 1.0 g of 1,3-dimethyl-6-[4-(3-hydroxypropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione (Compound a) and 1.06 g of triphenylphosphine, and 0.71 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 0.65 g of light yellow crystals. The crystals were recrystallized from ethanol to obtain 0.55 g of crystalline 1,3-dimethyl-6-[4-(3-[2-hydroxy-5-nitrophenyloxy]propyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione (Compound y).

Sources & evidence

ORD record
ord-5e6fa889999c49bba1b8ab57b6e47d94
Source dataset
uspto-grants-1994_07
Patent number
US05332739

Reaction notes

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