Triphenylphosphine → HCID 20061254, compound

HRID 1085281Notes

Reaction equation

HRID 1085281 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[OH:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][N:20]1[C:25]([NH:26][CH2:27][CH2:28][NH:29][C:30](=O)[C:31]2[CH:36]=CC([N+]([O-])=O)=CC=2)=[CH:24][C:23](=[O:41])[N:22]([CH3:42])[C:21]1=[O:43].[C:44]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:45]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:19][N:20]1[C:25]([N:26]2[CH2:27][CH2:28][N:29]([CH2:30][CH2:31][CH2:36][O:18][C:10]3[CH:11]=[CH:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][C:9]=3[NH:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:45][CH2:44]2)=[CH:24][C:23](=[O:41])[N:22]([CH3:42])[C:21]1=[O:43]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 20061251HCID 20061251, compound2×HCID 20061337HCID 20061337, compound

Product 1

HCID 20061254HCID 20061254, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.7 g of 2-benzylamino-4-nitrophenol, 0.8 g of 1,3-dimethyl-6-[4-(3-hydroxypropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione (Compound 139) and 0.9 g of triphenylphosphine were suspended in 20 ml of anhydrous tetrahydrofuran, followed by the addition of 0.65 g of diethyl azodicarboxylate. The thus-prepared mixture was treated in a similar manner to Example 84-(2), thereby obtaining 0.93 g of 1,3-dimethyl-6-{4-[3-(2-benzylamino-4-nitrophenyloxy)propyl]piperazin-1yl}-2,4(1H,3H)-pyrimidinedione as crystals.

Sources & evidence

ORD record
ord-dcb30a4711e2425fa2f0c9b165eb92f2
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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