Triethylamine → HCID 178516147, Verbindung

HRID 577255Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577255
Br.Br[CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[Cl:10].[SH:11][C:12]1[N:17]=[C:16]([OH:18])[CH:15]=[C:14]([C:19]([F:22])([F:21])[F:20])[N:13]=1.C(N(CC)CC)C>C(O)C>[Cl:10][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:4]=1[CH2:3][S:11][C:12]1[N:17]=[C:16]([OH:18])[CH:15]=[C:14]([C:19]([F:22])([F:20])[F:21])[N:13]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 668153214-(Bromomethyl)-3-chloropyridine hydrobromideHCID 178516148HCID 178516148, Verbindung

Produkt 1

HCID 178516147HCID 178516147, VerbindungAusbeute 54,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a 0° C. mixture of 4-(bromomethyl)-3-chloropyridine hydrobromide (7.2 mmol) and 2-sulfanyl-6-(trifluoromethyl)pyrimidin-4-ol (922 mg, 4.7 mmol) in absolute ethanol (40 mL) was added triethylamine (4.0 mL, 28.7 mmol). The mixture was stirred at room temperature overnight. The solid material was removed by filtration. Diethyl ether (2×50 mL) was used to wash the recovered solid. The solid material was removed by filtration. The filtrate was evaporated to dryness and then co-evaporated with ethyl acetate (1×25 mL). The solid residue was treated with water (100 mL). The solid product was recovered by filtration, washed with water (2×30 mL), diethyl ether (1×30 mL), and hexanes (2×30 mL), and was dried in vacuo to afford 2-{[(3-chloropyridin-4-yl)methyl]sulfanyl}-6-(trifluoromethyl)pyrimidin-4-ol (822 mg, 54%); 1H NMR (500 MHz, DMSO-d6): δ 4.50 (s, 2H), 6.66 (s, 1H), 7.58 (d, 1H, J=4.9 Hz), 8.47 (d, 1H, J=4.9 Hz), 8.64 (s, 1H); M+ 322.

Aufarbeitung

  1. customThe solid material was removed by filtration
  2. washto wash the recovered solid
  3. customThe solid material was removed by filtration
  4. customThe filtrate was evaporated to dryness
  5. additionThe solid residue was treated with water (100 mL)
  6. filtrationThe solid product was recovered by filtration
  7. washwashed with water (2×30 mL), diethyl ether (1×30 mL), and hexanes (2×30 mL)
  8. customwas dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-654216eb63b34aeba5903561a74e99bd
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040538B2

Notizen zur Reaktion

Wird geladen…