Triphenylphosphine → HCID 20061355, compound

HRID 1085275Notes

Reaction equation

HRID 1085275 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][N:16]1[C:21]([NH:22][CH2:23][CH2:24][NH:25][C:26](=O)[C:27]2[CH:32]=CC([N+]([O-])=O)=CC=2)=[CH:20][C:19](=[O:37])[N:18]([CH3:38])[C:17]1=[O:39].[C:40]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:41]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:15][N:16]1[C:21]([N:22]2[CH2:23][CH2:24][N:25]([CH2:26][CH2:27][CH2:32][O:1][C:2]3[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=3[N+:12]([O-:14])=[O:13])[CH2:41][CH2:40]2)=[CH:20][C:19](=[O:37])[N:18]([CH3:38])[C:17]1=[O:39]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 66835Benzoic acid, 4-hydroxy-3-nitro-, methyl esterHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 20061251HCID 20061251, compound2×

Product 1

HCID 20061355HCID 20061355, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.84 g of methyl 4-hydroxy-3-nitrobenzoate, 0.8 g of 1,3-dimethyl-6-[4-(3-hydroxypropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione (Compound 139) and 0.88 g of triphenylphosphine were suspended in 14 ml of anhydrous tetrahydrofuran, followed by the addition of 0.54 g of diethyl azodicarboxylate. The thus-prepared mixture was treated in a similar manner to Example 84-(2), thereby obtaining 1.1 g of 1,3-dimethyl-6-{4-[3-(4-methoxycarbonyl-2-nitrophenyloxy)propyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione as an oily substance.

Sources & evidence

ORD record
ord-830c11baa87941658a558e37c3dae742
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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