N,N'-Dicyclohexylurea → 1,4-dihydro-4-oxo-5-(phenylmethoxy)-N-(tetrahydro-2-oxo-1(2H)-pyrimidinyl)-2-pyridine-carboxamide

HRID 2351084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2351084
[O:1]=[C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][NH:5][C:4]([C:16]([OH:18])=O)=[CH:3]1.C1(N=C=NC2CCCCC2)CCCCC1.Cl.[NH2:35][N:36]1[CH2:41][CH2:40][CH2:39][NH:38][C:37]1=[O:42].C(N(CC)CC)C.C(NC1CCCCC1)(NC1CCCCC1)=O>CN(C)C=O.ON1C2C=CC=CC=2N=N1>[O:1]=[C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][NH:5][C:4]([C:16]([NH:35][N:36]2[CH2:41][CH2:40][CH2:39][NH:38][C:37]2=[O:42])=[O:18])=[CH:3]1

Komponenten

8

Edukt 5

HCID 4277N,N'-DicyclohexylureaHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 110539185-(Benzyloxy)-4-oxo-1,4-dihydropyridine-2-carboxylic acidHCID 1317161453-Aminotetrahydro-2(1H)-pyrimidinone, monohydrochloride

Produkt 1

HCID 198480031,4-dihydro-4-oxo-5-(phenylmethoxy)-N-(tetrahydro-2-oxo-1(2H)-pyrimidinyl)-2-pyridine-carboxamideAusbeute 128,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 757711-HydroxybenzotriazoleKatalysatorHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 4.7 g. (19.2 mmol) 1,4-dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinecarboxylic acid in 50 ml N,N-dimethylformamide was added 4.74 g (23 mmol) dicyclohexylcarbodiimide and 0.29 g (1.92 mmol) N-hydroxybenzotriazole. The mixture was stirred for 1 hour. To this was added a solution of 2.85 g (19.2 mmol) 3-aminotetrahydro-2(1H)-pyrimidinone, monohydrochloride and 1.94 g (19.2 mmol) triethylamine in 30 ml N,N-dimethylformamide. After stirring overnight the dicyclohexylurea was filtered off and the N,N-dimethylformamide evaporated in vacuo. The residue was triturated with ether to yield 8.47 g of the desired product (contained dicyclohexylurea). This crude material was used in the next step without further purification.

Aufarbeitung

  1. filtrationwas filtered off
  2. customthe N,N-dimethylformamide evaporated in vacuo
  3. customThe residue was triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-68cee8c2af8f4a8da017487511837cc9
Quelldatensatz
uspto-grants-1989_10
Patentnummer
US04871841

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