Triethylamine → HCID 178429440, Verbindung

HRID 629985Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 629985
[CH3:1][C:2]1[N:7]=[C:6]([SH:8])[N:5]=[C:4]([OH:9])[CH:3]=1.C(N(CC)CC)C.Br[CH2:18][C:19]1[C:20]([Cl:26])=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=1>C(O)C>[Cl:26][C:20]1[C:21]([OH:25])=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][S:8][C:6]1[N:5]=[C:4]([OH:9])[CH:3]=[C:2]([CH3:1])[N:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 59589404HCID 59589404, VerbindungHCID 178429541HCID 178429541, Verbindung

Produkt 1

HCID 178429440HCID 178429440, VerbindungAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

6-methyl-2-sulfanylpyrimidin-4-ol (152 mg, 1.1 mmol) was dissolved in absolute ethanol (8 mL), then triethylamine (140 μL, 1.0 mmol) and 3-(bromomethyl)-2-chlorophenol (200 mg, 0.9 mmol) were added. The mixture was stirred overnight at room temperature. The solid was removed by filtration, and the filtrate was evaporated. The residue was dissolved in DCM and purified on silica gel using 10% DCM/MeOH to afford 2-{[(2-chloro-3-hydroxyphenyl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (87 mg, 37% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.22 (s, 3H), 4.11 (bs, 1H), 4.44 (s, 2H), 5.99 (bs, 1H), 6.88-6.91 (m, 1H), 7.01-7.10 (m, 2H), 10.24 (bs, 1H); LRMS (ES+) m/z 283 (100%, M+1), 285 (50%, M+3).

Aufarbeitung

  1. customThe solid was removed by filtration
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in DCM
  4. custompurified on silica gel using 10% DCM/MeOH

Quellen und Nachweise

ORD-Eintrag
ord-e109d4f8878b434caef757d397ec9da4
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315521B2

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