4-Nitrophenol → 1,3-dimethyl-6-{4-[2-(4-nitrophenoxy)ethyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione

HRID 1729286Notes

Reaction equation

HRID 1729286 reaction equation
[CH3:1][N:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]2)=[CH:6][C:5](=[O:17])[N:4]([CH3:18])[C:3]1=[O:19].[N+:20]([C:23]1[CH:28]=[CH:27][C:26](O)=[CH:25][CH:24]=1)([O-:22])=[O:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:1][N:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:26]3[CH:27]=[CH:28][C:23]([N+:20]([O-:22])=[O:21])=[CH:24][CH:25]=3)[CH2:10][CH2:9]2)=[CH:6][C:5](=[O:17])[N:4]([CH3:18])[C:3]1=[O:19]

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 99702521,3-dimethyl-6-[4-(2-hydroxyethyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 100917261,3-dimethyl-6-{4-[2-(4-nitrophenoxy)ethyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedioneYield 69.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 100 ml of anhydrous tetrahydrofuran were added 5.37 g of 1,3-dimethyl-6-[4-(2-hydroxyethyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione, 3.20 g of 4-nitrophenol and 6.03 g of triphenylphosphine, and the resultant mixture and 50 ml of an anhydrous tetrahydrofuran solution containing 3.9 g of diethyl azodicarboxylate were treated in the same manner as in Reference Example 4, thereby obtaining 5.40 g of crystalline 1,3-dimethyl-6-[4-(2-[4-nitrophenoxy] ethyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione (Compound x).

Workup

  1. additionwere treated in the same manner as in Reference Example 4

Sources & evidence

ORD record
ord-a81f80c362af4be8bd06d0d76591e3b6
Source dataset
uspto-grants-1994_07
Patent number
US05332739

Reaction notes

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