Acetic Acid → 2-bromo-N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl-N'-methylbenzenesulfonimidamide

HRID 247001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 247001
N12CCCN=C1CCCCC2.[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19](=[N:22][CH3:23])([NH2:21])=[O:20].[CH3:24][O:25][C:26]1[CH:31]=[C:30]([O:32][CH3:33])[N:29]=[C:28]([NH:34][C:35](=[O:43])OC2C=CC=CC=2)[N:27]=1.C(O)(=O)C>C(#N)C.ClCCl>[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19](=[N:22][CH3:23])([NH:21][C:35]([NH:34][C:28]1[N:29]=[C:30]([O:32][CH3:33])[CH:31]=[C:26]([O:25][CH3:24])[N:27]=1)=[O:43])=[O:20]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 139209002-bromo-N'-methylbenzenesulfonimidamide

Produkt 1

HCID 139209012-bromo-N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl-N'-methylbenzenesulfonimidamideAusbeute 104,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1,8-Diazabicyclo[5.4.0]undec-7-ene (0.15 mL, 1.0 mmol) was added dropwise over one minute to a stirred solution of 2-bromo-N'-methylbenzenesulfonimidamide (0.25 g, 1.0 mmol) and phenyl (4,6-dimethoxypyrimidin-2-yl)carbamate (0.28 g, 1.0 mmol) in dry acetonitrile (5 mL) at room temperature. The solvent was evaporated, and the residue was dissolved in dichloromethane. Evaporation of this solvent left a pale yellow viscous oil (0.65 g). This was dissolved in CH2Cl2, and acetic acid (57 μL, 1.0 mol) was added. This solution was chromatographed on a column of silica gel using 1:1 dichloromethane-ether as eluant. Fractions containing the product were diluted with toluene. The solvent was evaporated leaving an oil. This was dissolved in dichloromethane, and the solvent was evaporated leaving 2-bromo-N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl-N'-methylbenzenesulfonimidamide as a hard amorphous foam (0.45 g) melting at 120°-125° C.

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. customEvaporation of this solvent
  4. waitleft a pale yellow viscous oil (0.65 g)
  5. dissolutionThis was dissolved in CH2Cl2
  6. customThis solution was chromatographed on a column of silica gel using 1:1 dichloromethane-ether as eluant
  7. additionFractions containing the product
  8. additionwere diluted with toluene
  9. customThe solvent was evaporated
  10. customleaving an oil
  11. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-08378ba26bce4d669dd358e1dc5e3e07
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04705555

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