Trityl chloride → Amino(1-triphenylmethyl-1,4,5,6-tetrahydropyrimidin-5-yl)acetamide

HRID 1653735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1653735
Cl.Cl.[NH2:3][CH:4]([CH:8]1[CH2:13][NH:12][CH:11]=[N:10][CH2:9]1)[C:5]([NH2:7])=[O:6].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1.[C:36](Cl)([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CN(C=O)C>[NH2:3][CH:4]([CH:8]1[CH2:13][N:12]([C:36]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:11]=[N:10][CH2:9]1)[C:5]([NH2:7])=[O:6]

Komponenten

5

Edukt 3

HCID 6456Trityl chlorideHCID 20080419Amino(1,4,5,6-tetrahydropyrimidine-5-yl)acetamide dihydrochlorideHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Produkt 1

HCID 20080439Amino(1-triphenylmethyl-1,4,5,6-tetrahydropyrimidin-5-yl)acetamideAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Amino(1,4,5,6-tetrahydropyrimidine-5-yl)acetamide dihydrochloride (1.33 g, 5.8 mmol), diazabicycloundecene (DBU, 2.6 ml, 17.4 mmol), and tritylchloride (1.61 g, 5.8 mmol) are dissolved in anhydrous DMF (20 ml) with stirring under nitrogen at room temperature. After 18 hours stirring the suspension is evaporated in vacuo, and the residue chromatographed (silica, chloroform/methanol, 9:1) to yield 1.64 g (71%) white crystalline solid, identified by 300 MHz nmr and ms m/z=398.

Aufarbeitung

  1. stirringAfter 18 hours stirring the suspension
  2. customis evaporated in vacuo
  3. customthe residue chromatographed (silica, chloroform/methanol, 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-ece439652bcf4c84a0aff3ca8de15e3f
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05403845

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