4-Methylphenyl isocyanate → 4-(5-Amino-2-(pyridin-3-yl)thiazolo[5,4-d]pyrimidin-7-yl)-N-(p-tolyl)piperazine-1-carboxamide

HRID 718270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 718270
[NH2:1][C:2]1[N:3]=[C:4]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[C:5]2[N:10]=[C:9]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[S:8][C:6]=2[N:7]=1.[C:23]1([CH3:32])[CH:28]=[CH:27][C:26]([N:29]=[C:30]=[O:31])=[CH:25][CH:24]=1>O1CCOCC1>[NH2:1][C:2]1[N:3]=[C:4]([N:17]2[CH2:18][CH2:19][N:20]([C:30]([NH:29][C:26]3[CH:27]=[CH:28][C:23]([CH3:32])=[CH:24][CH:25]=3)=[O:31])[CH2:21][CH2:22]2)[C:5]2[N:10]=[C:9]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[S:8][C:6]=2[N:7]=1

Komponenten

4

Edukt 2

HCID 693254-Methylphenyl isocyanateHCID 509420567-(Piperazin-1-yl)-2-(pyridin-3-yl)thiazolo[5,4-d]pyrimidin-5-amine

Produkt 1

HCID 469163824-(5-Amino-2-(pyridin-3-yl)thiazolo[5,4-d]pyrimidin-7-yl)-N-(p-tolyl)piperazine-1-carboxamideAusbeute 79,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a suspension of 5-amino-7-(piperazin-1-yl)-2-(pyridine-3-yl)thiazolo[5,4-d]pyrimidine (150 mg, 0.48 mmol) in dioxane (10 ml) was added 4-tolyl isocyanate (63 μl, 0.5 mmol). The resulting reaction mixture was stirred at room temperature for 30 minutes. The solvents were evaporated in vacuo and the residue was purified by flash chromatography on silica, the mobile phase being a mixture of methanol and dichloromethane (in a ratio of 1/25), yielding the pure title compound as a yellowish solid (170 mg, 79%).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customThe solvents were evaporated in vacuo
  3. customthe residue was purified by flash chromatography on silica
  4. additiona mixture of methanol and dichloromethane (in a ratio of 1/25),

Quellen und Nachweise

ORD-Eintrag
ord-9e1be929a6454bfea2259600a36d84a2
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193741B2

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