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

HRID 1681903Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1681903
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-1521d6b8182b4267b523d3cb220fc94c
Quelldatensatz
uspto-grants-1992_12
Patentnummer
US05175166

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