Triethylamine → 6-Benzyloxyamino-4-chloro-2,5-diformamidopyrimidine

HRID 6253

Reaktionsgleichung

Reaktionsgleichung von HRID 6253
Cl[C:2]1[C:7]([NH:8][CH:9]=[O:10])=[C:6]([Cl:11])[N:5]=[C:4]([NH:12][CH:13]=[O:14])[N:3]=1.[CH2:15]([O:22][NH2:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>O1CCOCC1>[CH2:15]([O:22][NH:23][C:2]1[N:3]=[C:4]([NH:12][CH:13]=[O:14])[N:5]=[C:6]([Cl:11])[C:7]=1[NH:8][CH:9]=[O:10])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 102313O-BenzylhydroxylamineHCID 13989892N-(4,6-dichloro-2-formamido-pyrimidin-5-yl)formamide

Produkt 1

HCID 145239606-Benzyloxyamino-4-chloro-2,5-diformamidopyrimidineAusbeute 46,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4,6-dichloro-2,5-diformamido-pyrimidine (1.9 g, 8.09 mmol), benzyloxyamine (1 g, 8.13 mmol), triethylamine (2 ml) and dioxan (20 ml) was stirred at 100° C. for 1 hour. The cooled reaction mixture was filtered and the precipitate collected and washed with dioxan (2×5 ml). The filtrate and washings were combined and evaporated to a syrup. Column chromatography on silica gel (eluted with chloroform-ethanol, 30:1) afforded the title compound (1.2 g, 46%). IR: νmax (KBr) 3242, 1694, 1588, 1472 cm-1 ; 1H NMR δH [(CD3)2SO], 4.89 (2H, s, OCH2Ph), 7.4 (5H, m, Ph), 8.15 (1H, s, CHO), 9.18, 9.42 (1H, 2×br.s, D2O exchangeable, NH), 9.25 (1H, br.s, CHO), 10.91 (2H, br.s, D2O exchangeable, 2×NH). m/z (FAB+ve ion, thioglycerol) MH+ 322.

Aufarbeitung

  1. customThe cooled reaction mixture
  2. filtrationwas filtered
  3. customthe precipitate collected
  4. washwashed with dioxan (2×5 ml)
  5. customevaporated to a syrup

Quellen und Nachweise

ORD-Eintrag
ord-44cf70cb0643481db455beee7bccf37f
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05247085

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