Methanol → 6-(2-Chloro-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one

HRID 41522

Reaktionsgleichung

Reaktionsgleichung von HRID 41522
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.[Cl:12][C:13]1[N:18]=[C:17](Cl)[C:16]([CH3:20])=[CH:15][N:14]=1.CO>O>[Cl:12][C:13]1[N:18]=[C:17]([NH:1][C:2]2[CH:11]=[CH:10][C:5]3[NH:6][C:7](=[O:9])[O:8][C:4]=3[CH:3]=2)[C:16]([CH3:20])=[CH:15][N:14]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 74508Pyrimidine, 2,4-dichloro-5-methyl-HCID 8269896-amino-1,3-benzoxazol-2(3H)-one

Produkt 1

HCID 866436446-(2-Chloro-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-oneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a vial with 6-aminobenzo[d]oxazol-2(3H)-one (1.0 g, 6.7 mmol) and 2,4-dichloro-5-methylpyrimidine (1.4 g, 8.7 mmol), solvents MeOH (20 mL) and H2O (5 mL) were added. The turbid mixture was stirred at room temperature for 2 days. Precipitate from the reaction mixture was collected by filtration, washing with H2O (3 mL×2) and EtOAc (3 mL×2), and was further drying in vacuo. 6-(2-Chloro-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one was obtained as a light tan color solid: 1.59 g (86% yield); 1H NMR (300 MHz, DMSO) δ 11.59 (s, 1H), 8.87 (s, 1H), 7.99 (s, 1H), 7.56 (s, 1H), 7.28 (d, J=8.3, 1H), 7.06 (d, J=8.3, 1H), 2.14 (s, 3H).

Aufarbeitung

  1. filtrationPrecipitate from the reaction mixture was collected by filtration
  2. washwashing with H2O (3 mL×2) and EtOAc (3 mL×2)
  3. customwas further drying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-53cdf6963ff5438598820bc53247ac23
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530656B2

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