Triethylamine → 5-Methyl-4-((3-phenyl-isoxazol-5-yl)-methoxy-)-thieno[2,3-d]pyrimidine

HRID 57779Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 57779
Cl[C:2]1[C:3]2[CH:10]=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[OH:11][CH2:12][C:13]1[O:17][N:16]=[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=1.[CH2:24](N(CC)CC)C>C(O)(C)C>[CH3:24][C:10]1[C:3]2[C:2]([O:11][CH2:12][C:13]3[O:17][N:16]=[C:15]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:14]=3)=[N:7][CH:6]=[N:5][C:4]=2[S:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 7366184-Chlorothieno[2,3-d]pyrimidineHCID 2763417(3-Phenyl-5-isoxazolyl)methanol

Produkt 1

HCID 734426745-Methyl-4-((3-phenyl-isoxazol-5-yl)-methoxy-)-thieno[2,3-d]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel2×

Versuchsvorschrift

0.184 g (1 mmol) of 4-chloro-thieno[2,3-d]pyrimidine was dissolved in 5 ml of dry isopropanol. A solution of 0.175 g (1 mmol) of 5-hydroxymethyl-3-phenyl-isoxazole in 5 ml isopropanol was slowly added dropwise into the reaction system, followed by the addition of 0.101 g (1 mmol) freshly distilled triethylamine. The system was stirred at room temperature for 30 min and then was reacted at 60. After the completion of the reaction monitored by TLC, the reaction solution was concentrated under vacuum. The residue was directly separated on (V(petroleum ether):V(ethyl acetate)=9:1-4:1) to give the target compound of 5-methyl-4-((3-phenyl-isoxazol-5-yl)-methoxy-)-thieno[2,3-d]pyrimidine (named S-1 in the following Table). The other compounds were synthesized according to the synthetic process of 5-methyl-4-((3-phenyl-isoxazol-5-yl)-methoxy-)-thieno[2,3-d]pyrimidine. Their structures were determined by analytical methods of IR, 1H NMR, ESI-MS, etc. The physical constants and spectral data of preferred compounds were illustrated in the form of table.

Aufarbeitung

  1. customwas reacted at 60
  2. concentrationthe reaction solution was concentrated under vacuum
  3. customThe residue was directly separated on (V(petroleum ether):V(ethyl acetate)=9:1-4:1)

Quellen und Nachweise

ORD-Eintrag
ord-5777f72ff95242d3a6dc2f98fb9c0e37
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434741B2

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