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Water → 3-(Benzyloxy)-10,10-dimethyl-4-oxo-6,7,8,10-tetrahydro-4H-pyrimido[2,1-c][1,4]oxazepine-2-carboxylic acid

HRID 348118
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 348118
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]([C:9]1[NH:10][C:11](=[O:21])[C:12]([OH:20])=[C:13]([C:15]([O:17]CC)=[O:16])[N:14]=1)([CH3:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.O>CN(C)C=O>[CH2:28]([O:20][C:12]1[C:11](=[O:21])[N:10]2[C:9]([C:6]([CH3:7])([CH3:8])[O:5][CH2:4][CH2:3][CH2:2]2)=[N:14][C:13]=1[C:15]([OH:17])=[O:16])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 135848641Ethyl 2-(2-(3-chloropropoxy)propan-2-yl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate

Produkt 1

HCID 210698553-(Benzyloxy)-10,10-dimethyl-4-oxo-6,7,8,10-tetrahydro-4H-pyrimido[2,1-c][1,4]oxazepine-2-carboxylic acidAusbeute 135,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A suspension of intermediate 33, ethyl 2-(2-(3-chloropropoxy)propan-2-yl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate, (0.205 g, 0.64 mmol) and anhydrous potassium carbonate (0.361 g, 2.6 mmol) in anhydrous dimethylformamide (4 mL) was stirred at 60° C. for 5 hours. The reaction mixture was treated with benzyl bromide (0.122 g, 0.71 mmol) and stirred for 16 hours. Following this, 2 mL of H2O was added and the mixture stirred for an additional 24 hours. Solvent was removed by rotary evaporator and the resulting residue suspended in 0.5 N hydrochloric acid (16 mL). The crude product was extracted with ethyl acetate (2×15 mL), then dried (sodium sulfate), filtered, and concentrated to dryness by rotary evaporator to give 0.299 g (Yield>100%) of the title compound as a solid. LC/MS [M+H]+=345.21.

Aufarbeitung

  1. stirringstirred for 16 hours
  2. additionwas added
  3. stirringthe mixture stirred for an additional 24 hours
  4. customSolvent was removed by rotary evaporator
  5. extractionThe crude product was extracted with ethyl acetate (2×15 mL)
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated to dryness by rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-ac345fc9fe5348a2a5d3d2b1309ee2c0
Quelldatensatz
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07176196B2

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