Bromoacetyl bromide → 2-bromo-N-(6-chloro-2-phenylpyrimidin-4-yl)acetamide

HRID 1783328

Reaktionsgleichung

Reaktionsgleichung von HRID 1783328
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([NH2:14])[CH:3]=1.[Br:15][CH2:16][C:17](Br)=[O:18].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Br:15][CH2:16][C:17]([NH:14][C:4]1[CH:3]=[C:2]([Cl:1])[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=1)=[O:18]

Komponenten

5

Edukt 3

HCID 61147Bromoacetyl bromideHCID 81531DiisopropylethylamineHCID 3177476-Chloro-2-phenylpyrimidin-4-amine

Produkt 1

HCID 223791512-bromo-N-(6-chloro-2-phenylpyrimidin-4-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

6-chloro-2-phenylpyrimidin-4-amine (4) (830 mg) was dissolved in anhydrous DCM (50 ml). To this was added dropwise a solution of bromoacetylbromide (1.05 ml in 10 ml DCM), forming a precipitate after 10 min. To this was then added dropwise a solution of N,N-diisopropylethylamine (1.06 ml in 10 ml DCM) and the solution left for 1 hr. The solvent was removed in vacuo, then the crude solid purified by flash chromatography on silica gel eluting with a mixture of ethyl acetate and petroleum ether (1:9 then 1:1 v/v), furnishing the title compound as a solid (1.09 g).

Aufarbeitung

  1. customforming a precipitate after 10 min
  2. customThe solvent was removed in vacuo
  3. customthe crude solid purified by flash chromatography on silica gel eluting with a mixture of ethyl acetate and petroleum ether (1:9

Quellen und Nachweise

ORD-Eintrag
ord-40dfc95fe54d4561abf036588c7acd5a
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07501407B2

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