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Sodium hydride → 1-Triphenylmethyl-1,4,5,6-tetrahydro-5-(3-n-pentyl-1,2,4-oxadiazol-5-yl)pyrimidine

HRID 1681908
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1681908
[H-].[Na+].[C:3](=[N:10][OH:11])([NH2:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:12]1([C:18]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:19]2[CH2:24][CH:23]([C:25](OC)=O)[CH2:22][N:21]=[CH:20]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[C:35]1([C:18]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:19]2[CH2:24][CH:23]([C:25]3[O:11][N:10]=[C:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[N:9]=3)[CH2:22][N:21]=[CH:20]2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 3613628N'-hydroxyhexanimidamideHCID 100455711-Triphenylmethyl-5-methoxycarbonyl-1,4,5,6-tetrahydropyrimidine

Produkt 1

HCID 103443951-Triphenylmethyl-1,4,5,6-tetrahydro-5-(3-n-pentyl-1,2,4-oxadiazol-5-yl)pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel
2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Prepared by a procedure similar to Example 9, where sodium hydride (95% 40 mg, 1.7 mmol) and n-hexanamidoxime (217 mg, 1.7 mmol) were suspended in dry THF in an oven dried round bottom flask with stirring under nitrogen at 0° C. After 15 minutes stirring the ice bath was removed and the grey suspension refluxed 45 minutes to give a white suspension. 1-Triphenylmethyl-1,4,5,6-tetrahydro-5-methoxycarbonylpyrimidine (640 mg, 1.7 mmol) was added, dissolved in dry THF and reflux continued 18 hours. The solvents were evaporated in vacuo and the residue was chromatographed (silica, chloroform/methanol, 9:1) to yield 1-triphenylmethyl-1,4,5,6-tetrahydro-5-(3-n-pentyl-1,2,4-oxadiazol-5-yl)pyrimidine. This product was dissolved in triflouroacetic acid (2 mL), with stirring at room temperature for 24 hours. The yellow solution was then evaporated in vacuo, and the residue recrystallized from methanol/ether to yield 110 mg (19%) white crystals, mp 97°-99° C. identified by 300 MHz nmr.

Aufarbeitung

  1. customdried round bottom flask
  2. stirringAfter 15 minutes stirring the ice bath
  3. customwas removed
  4. temperaturethe grey suspension refluxed 45 minutes
  5. customto give a white suspension
  6. temperaturereflux
  7. customThe solvents were evaporated in vacuo
  8. customthe residue was chromatographed (silica, chloroform/methanol, 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-37ac5ad644f144b185c660d9b3be21bc
Quelldatensatz
uspto-grants-1992_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05175166

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