N-bromobutanimide → 2-Bromo-1-(2-cyclopropylmethoxypyrimidin-5-yl)ethanone

HRID 633733Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 633733
[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[CH:10][C:9]([C:12]([O:14]CC)=[CH2:13])=[CH:8][N:7]=2)[CH2:3][CH2:2]1.[Br:17]N1C(=O)CCC1=O>C1COCC1.O.C(OCC)(=O)C>[Br:17][CH2:14][C:12]([C:9]1[CH:8]=[N:7][C:6]([O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)=[N:11][CH:10]=1)=[O:13]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 1181998532-Cyclopropylmethoxy-5-(1-ethoxyvinyl)pyrimidine

Produkt 1

HCID 1181998522-Bromo-1-(2-cyclopropylmethoxypyrimidin-5-yl)ethanoneAusbeute 71,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 21881883Oxolane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 480 mg (2.18 mmol) of 2-cyclopropylmethoxy-5-(1-ethoxyvinyl)pyrimidine in 8 mL of a THF/H2O mixture: (6/2: v/v) is cooled to 0° C. under argon. After addition of 380.02 mg (2.11 mmol) of N-bromosuccinimide, the reaction mixture is maintained at 0° C. for 1 hour. The solution obtained is taken up in ethyl acetate and washed with aqueous NaHCO3 solution and then with saturated NaCl solution. The organic phase is dried over magnesium sulfate and evaporated to dryness. The residue is purified by chromatography on silica gel (eluent: 80/20 DCM/MeOH) to give 410 mg of 2-bromo-1-(2-cyclopropylmethoxypyrimidin-5-yl)ethanone, the characteristics of which are as follows:

Aufarbeitung

  1. customThe solution obtained
  2. washwashed with aqueous NaHCO3 solution
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe residue is purified by chromatography on silica gel (eluent: 80/20 DCM/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-9372a79e407c4764adbbc7f5b1a76598
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321790B2

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