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tert-Butanol → (2-Methylsulfanyl-4-o-tolyl-pyrimidin-5-yl)-carbamic acid tert.-butyl ester

HRID 650637
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 650637
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[C:6](C(O)=O)=[CH:5][N:4]=1.C([N:21]([CH2:24]C)CC)C.[C:26]([OH:30])([CH3:29])([CH3:28])[CH3:27].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:38])C=CC=CC=1>C1COCC1>[C:26]([O:30][C:24](=[O:38])[NH:21][C:6]1[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[N:8][C:3]([S:2][CH3:1])=[N:4][CH:5]=1)([CH3:29])([CH3:28])[CH3:27]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 217124342-Methylsulfanyl-4-o-tolyl-pyrimidine-5-carboxylic acid

Produkt 1

HCID 20677557(2-Methylsulfanyl-4-o-tolyl-pyrimidin-5-yl)-carbamic acid tert.-butyl esterAusbeute 65,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2.33 g (8.95 mmol) 2-methylsulfanyl-4-o-tolyl-pyrimidine-5-carboxylic acid, 1.25 ml triethylamine (8.95 mmol) and 1.68 ml (17.9 mmol) t-butanol in 30 ml THF, 1.97 ml (8.95 mmol) diphenylphosphorylazide were added and the resulting solution heated at reflux for 12 hrs. After evaporation of the solvent, the residue was distributed between CH2Cl2 and H2O. The aqueous phase was extracted twice with CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 15:1) to give 1.95 g (65%) (2-methylsulfanyl-4-o-tolyl-pyrimidin-5-yl)-carbamic acid tert.-butyl ester as a colorless solid, MS (TSP): 331 (M+).

Aufarbeitung

  1. temperaturethe resulting solution heated
  2. temperatureat reflux for 12 hrs
  3. customAfter evaporation of the solvent
  4. extractionThe aqueous phase was extracted twice with CH2Cl2
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate 15:1)

Quellen und Nachweise

ORD-Eintrag
ord-c6a7bb57e1334be6b70076fa9b7f9c31
Quelldatensatz
uspto-grants-2001_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06274588B1

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