Barbituric Acid → rel-(2R,4R,4aR)-1,2,4,4a-tetrahydro-4-methyl-8-nitro-2-(trifluoromethyl)spiro[[1,4]oxazino[4,3-a]quinoline-5(6H), 5'(2'H)-pyrimidine]-2',4',6'(1'H,3'H)-trione

HRID 1966324Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1966324
[CH3:1][C@H:2]1[O:7][C@@H:6]([C:8]([F:11])([F:10])[F:9])[CH2:5][N:4]([C:12]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:13]=2[CH:14]=O)[CH2:3]1.[NH:23]1[C:30](=[O:31])[CH2:29][C:27](=[O:28])[NH:26][C:24]1=[O:25]>CO>[CH3:1][C@@H:2]1[C@H:3]2[C:29]3([CH2:14][C:13]4[C:12]([N:4]2[CH2:5][C@H:6]([C:8]([F:10])([F:9])[F:11])[O:7]1)=[CH:19][CH:18]=[C:17]([N+:20]([O-:22])=[O:21])[CH:16]=4)[C:27](=[O:28])[NH:26][C:24](=[O:25])[NH:23][C:30]3=[O:31]

Komponenten

4

Edukt 2

HCID 6211Barbituric AcidHCID 588470172-[cis-2-Methyl-6-(trifluoromethyl)morpholin-4-yl]-5-nitrobenzaldehyde

Produkt 1

HCID 68524841rel-(2R,4R,4aR)-1,2,4,4a-tetrahydro-4-methyl-8-nitro-2-(trifluoromethyl)spiro[[1,4]oxazino[4,3-a]quinoline-5(6H), 5'(2'H)-pyrimidine]-2',4',6'(1'H,3'H)-trione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2-[cis-2-methyl-6-(trifluoromethyl)morpholin-4-yl]-5-nitrobenzaldehyde (212 mg, 0.67 mol) is combined with barbituric acid (95 mg, 0.67 mmol, Aldrich) in a vial with MeOH (3 mL). The sealed reaction is heated to 80° C. on a shaker block for 21 hours and then the solvent is removed by rotary evaporation. The product is purified on a Biotage Flash 25M+ using a 26 minute linear gradient of 2.5%-10% MTBE in CH2Cl2 eluent. The product is dried under vacuum yielding a yellow-orange solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.01, 2.93, 3.46, 3.66, 3.73, 4.04, 4.40, 4.48, 7.10, 7.88, 8.01, 11.63, 11.94.

Aufarbeitung

  1. customThe sealed reaction
  2. customthe solvent is removed by rotary evaporation
  3. customThe product is purified on a Biotage Flash 25M+
  4. customThe product is dried under vacuum
  5. customyielding a yellow-orange solid

Quellen und Nachweise

ORD-Eintrag
ord-9f41eea4ceb7449ca8143b3e7c86be62
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420646B2

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