Trityl chloride → 1-Triphenylmethyl-5-methoxycarbonyl-1,4,5,6-tetrahydropyrimidine

HRID 1653710

Reaktionsgleichung

Reaktionsgleichung von HRID 1653710
Cl.[CH3:2][O:3][C:4]([CH:6]1[CH2:11][NH:10][CH:9]=[N:8][CH2:7]1)=[O:5].N12CCCN=C1CCCCC2.[C:23](Cl)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[C:24]1([C:23]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:8]2[CH2:7][CH:6]([C:4]([O:3][CH3:2])=[O:5])[CH2:11][N:10]=[CH:9]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Komponenten

5

Edukt 3

HCID 6456Trityl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199620591,4,5,6-Tetrahydro-5-methoxycarbonylpyrimidine Hydrochloride

Produkt 1

HCID 100455711-Triphenylmethyl-5-methoxycarbonyl-1,4,5,6-tetrahydropyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1,4,5,6-Tetrahydro-5-methoxycarbonylpyrimidine hydrochloride (1.49 g, 8.3 mmol) , 1,8 diazabicyclo [5.4.0] undec-7ene, (hereinafter diazabicycloundecene and/or DBU), (2.5 mL, 16.6 mmol), and tritylchloride (2.32 g, 8.3 mmol) were suspended in anhydrous DMF (20 ml) with stirring under nitrogen at room temperature. After 18 hours stirring the suspension was evaporated in vacuo and the residue chromatographed (silica, chloroform/methanol, 9:1) to yield 2.28 g (rf=0.15, 71%)white crystalline solid identified by 300 MHz nmr and ms m/z=384.

Aufarbeitung

  1. stirringAfter 18 hours stirring the suspension
  2. customwas evaporated in vacuo
  3. customthe residue chromatographed (silica, chloroform/methanol, 9:1)
  4. customto yield 2.28 g (rf=0.15, 71%)white crystalline solid

Quellen und Nachweise

ORD-Eintrag
ord-d701dcc8b3bd447c89a728af87a1f7a1
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05403845

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