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Carbon Dioxide → [4-(2-Methoxy-ethyl)-6-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol

HRID 890469
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 890469
CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.C(=O)=O.C[O:21][C:22]([C:24]1[C:25]([CH2:41][CH2:42][O:43][CH3:44])=[N:26][C:27]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=2)=[N:28][C:29]=1[CH3:30])=O>O1CCCC1>[CH3:44][O:43][CH2:42][CH2:41][C:25]1[C:24]([CH2:22][OH:21])=[C:29]([CH3:30])[N:28]=[C:27]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=2)[N:26]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 280Carbon DioxideHCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 670723194-(2-Methoxy-ethyl)-6-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid methyl ester

Produkt 1

HCID 21935907[4-(2-Methoxy-ethyl)-6-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanolAusbeute 103,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

A 1.2 M solution of DIBALH in toluene (34.6 ml, 41.5 mmol) was added dropwise to a dry-ice cooled solution of 4-(2-methoxy-ethyl)-6-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid methyl ester (4.9 g, 13.8 mmol) in tetrahydrofuran (50 ml). The reaction mixture was stirred for 15 min at −70° C., the dry-ice bath was removed and the reaction temperature was allowed to come to RT. The reaction mixture was stirred for 2 h at RT. Under ice-cooling 6 N aqueous HCl (10 ml) was carefully added. After 4 min ether was added, the layers were separated and the organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure to give 4.67 g (14.3 mmol, quant.) of crystalline [4-(2-methoxy-ethyl)-6-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol.

Aufarbeitung

  1. customthe dry-ice bath was removed
  2. customto come to RT
  3. stirringThe reaction mixture was stirred for 2 h at RT
  4. temperatureUnder ice-cooling 6 N aqueous HCl (10 ml)
  5. additionwas carefully added
  6. additionAfter 4 min ether was added
  7. customthe layers were separated
  8. washthe organic layer was washed with water
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f1be82090dc9466ea2abacdd59029b69
Quelldatensatz
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06995263B2

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