Phenol → 6-(4-Chlorophenyl)-3-({6-[(1-methylpiperidin-4-yl)oxy]pyridin-2-yl}methyl)thieno[3,2-d]pyrimidin-4(3H)-one

HRID 2239338Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2239338
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13]([O:15]C)=O)=[C:10](/[N:17]=[CH:18]/[N:19]([CH3:21])C)[CH:9]=2)=[CH:4][CH:3]=1.[CH3:22][N:23]1[CH2:28][CH2:27][CH:26]([O:29][C:30]2[N:35]=[C:34](CN)[CH:33]=[CH:32][CH:31]=2)[CH2:25][CH2:24]1.C1(O)C=CC=CC=1>C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]3[C:13](=[O:15])[N:19]([CH2:21][C:34]4[CH:33]=[CH:32][CH:31]=[C:30]([O:29][CH:26]5[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]5)[N:35]=4)[CH:18]=[N:17][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 996PhenolHCID 622878781-{6-[(1-Methylpiperidin-4-yl)oxy]pyridin-2-yl}methanamineHCID 178499302HCID 178499302, Verbindung

Produkt 1

HCID 247858026-(4-Chlorophenyl)-3-({6-[(1-methylpiperidin-4-yl)oxy]pyridin-2-yl}methyl)thieno[3,2-d]pyrimidin-4(3H)-oneAusbeute 33,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

Methyl 5-(4-chlorophenyl)-3-{[(1E)-(dimethylamino)methylene]amino}thiophene-2-carboxylate (1.39 g, 4.29 mmol) and 1-{6-[(1-methylpiperidin-4-yl)oxy]pyridin-2-yl}methanamine (0.950 g, 4.29 mmol, from step b above) were mixed with 4 g of phenol and heated to 130° C. on an oil bath for 1 h. When the mixture had cooled down it was diluted with 150 mL of diethyl ether. The mixture became opaque and left overnight. Very little had precipitated but when evaporation of ether was commenced much precipitate was formed and filtered off. The material was recrystallized from ethanol, filtered, washed with ethanol and dried to give 0.675 g (32%) of the desired compound. Mp 202-203° C. 1H NMR (600 MHz, CD3OD) δ 8.43 (s, 1H), 7.75 (m, 2H), 7.65 (s, 1H), 7.60 (t, 1H), 7.45 (m, 2H), 6.95 (d, 1H), 6.55 (d, 1H), 5.30 (s, 2H), 4.55 (br, 1H), 2.52 (m, 2H), 2.05 (s, 3H), 1.84 (m, 2H), 1.70 (m, 2H), 1.51 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 162.7, 157.9, 157.0, 151.9, 151.6, 149.1, 140.1, 135.9, 131.7, 129.7, 127.9, 123.0, 121.1, 115.7, 111.2, 51.4, 50.3, 44.6, 28.7, 22.1. MS (ESI+) 467/469 (M+1H+).

Aufarbeitung

  1. temperatureWhen the mixture had cooled down it
  2. customVery little had precipitated
  3. customwhen evaporation of ether
  4. customwas formed
  5. filtrationfiltered off
  6. customThe material was recrystallized from ethanol
  7. filtrationfiltered
  8. washwashed with ethanol
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-572cc26249224b37a7bf3c2258079c8c
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723331B2

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