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1,1'-Carbonyldiimidazole → HCID 53633805, Verbindung

HRID 974775
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 974775
[C:1]([N:8]1[CH2:14][CH2:13][CH2:12][C@H:9]1[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:15](N1C=CN=C1)(N1C=CN=C1)=[O:16].[N:27]1([C:32]2[N:37]=[C:36]([N:38]3[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]3)[CH:35]=[C:34]([N:44]3[CH2:48][CH2:47][CH2:46][CH2:45]3)[N:33]=2)[CH2:31][CH2:30][CH2:29][CH2:28]1.P([O-])(O)(O)=O.[Na+]>C1COCC1>[C:4]([O:3][C:1]([N:8]1[CH2:14][CH2:13][CH2:12][CH:9]1[CH2:10][O:11][C:15]([N:41]1[CH2:42][CH2:43][N:38]([C:36]2[CH:35]=[C:34]([N:44]3[CH2:45][CH2:46][CH2:47][CH2:48]3)[N:33]=[C:32]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[N:37]=2)[CH2:39][CH2:40]1)=[O:16])=[O:2])([CH3:7])([CH3:6])[CH3:5]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 682631,1'-CarbonyldiimidazoleHCID 643448(S)-(-)-N-Boc-prolinolHCID 145852434-(Piperazin-1-yl)-2,6-di(pyrrolidin-1-yl)pyrimidineHCID 23672064Monosodium phosphate

Produkt 1

HCID 53633805HCID 53633805, VerbindungAusbeute 69,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

A solution of 3 g of BOC-(L)-prolinol in 100 ml of anhydrous THF, cooled at 0° C. with water/ice, under stirring and inert gas atmosphere, is added with 2.9 g of carbonyldiimidazole in portions, then the reaction mixture is warmed to room temperature and stirring is continued for 3 hours. Said solution is added with 4.5 g of N-[2,6-bis(pyrrolidin-1-yl)pyrimidin-4-yl]piperazine in portions and stirring is continued for 18 hours. The reaction mixture is added with 400 ml of an aqueous saturated solution of sodium dihydrogen phosphate and extracted with ethyl acetate (3×100 ml). The combined organic extracts are dried over sodium sulfate and the solvent is evaporated off under reduced pressure. The residue (7.5 g) is purified by silica gel chromatography (eluent hexane/ethyl acetate 7:3), to obtain 5.5 g of (-)-N'-[(1-(tertbutoxycarbonyl) pyrrolidin-2-yl) methyloxycarbonyl]-N-[2,6-bis(pyrrolidin -1-yl)pyrimidin -4 -yl]piperazine, m.p. 147° C., [(α]D-32'(c=0.25 in EtOH).

Aufarbeitung

  1. stirringstirring
  2. stirringstirring
  3. waitis continued for 18 hours
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. dry with materialThe combined organic extracts are dried over sodium sulfate
  6. customthe solvent is evaporated off under reduced pressure
  7. customThe residue (7.5 g) is purified by silica gel chromatography (eluent hexane/ethyl acetate 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-88e3e0aed66c403d849bbae06b643840
Quelldatensatz
uspto-grants-1997_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05607930

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