Triethylamine → HCID 178429441, Verbindung

HRID 576986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 576986
Br[CH2:2][C:3]1[CH:7]=[C:6]([Cl:8])[S:5][C:4]=1[Cl:9].[CH3:10][C:11]1[N:16]=[C:15]([SH:17])[N:14]=[C:13]([OH:18])[CH:12]=1.C(N(CC)CC)C>C(O)C>[Cl:9][C:4]1[S:5][C:6]([Cl:8])=[CH:7][C:3]=1[CH2:2][S:17][C:15]1[N:14]=[C:13]([OH:18])[CH:12]=[C:11]([CH3:10])[N:16]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 234340823-(Bromomethyl)-2,5-dichlorothiopheneHCID 178429541HCID 178429541, Verbindung

Produkt 1

HCID 178429441HCID 178429441, VerbindungAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 3-(bromomethyl)-2,5-dichlorothiophene (125 mg, 0.51 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (60 mg, 0.42 mmol), and triethylamine (180 μL, 1.3 mmol) in absolute ethanol (5 mL) was stirred at room temperature overnight. The mixture was recovered and evaporated. The solid residue was treated with water (100 mL). The solid product was recovered by filtration, washed with water (1×15 mL), diethyl ether (2×15 mL), and hexanes (2×15 mL), and then dried in vacuo, affording 2-{[(2,5-dichlorothiophen-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (91 mg, 71% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.21 (s, 3H), 4.27 (s, 2H), 6.02 (s (br), 1H), 7.17 (s 1H); M+ 308.

Aufarbeitung

  1. customThe mixture was recovered
  2. customevaporated
  3. additionThe solid residue was treated with water (100 mL)
  4. filtrationThe solid product was recovered by filtration
  5. washwashed with water (1×15 mL), diethyl ether (2×15 mL), and hexanes (2×15 mL)
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a2970eda6e5844beb480582f5f65a4b5
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040538B2

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