Water → 5-chloro-N-(3-(methylsulfonyl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine

HRID 1410045

Reaktionsgleichung

Reaktionsgleichung von HRID 1410045
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1.[CH3:12][S:13]([C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19])(=[O:15])=[O:14].CCN(C(C)C)C(C)C.O>CS(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:19][C:18]2[CH:20]=[CH:21][CH:22]=[C:16]([S:13]([CH3:12])(=[O:15])=[O:14])[CH:17]=2)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 4280293-(Methylsulphonyl)anilineHCID 6096395,7-Dichlorothiazolo(5,4-d)pyrimidine

Produkt 1

HCID 866717835-chloro-N-(3-(methylsulfonyl)phenyl)thiazolo[5,4-d]pyrimidin-7-amineAusbeute 66,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixture of 5,7-dichlorothiazolo[5,4-d]pyrimidine (200 mg, 0.97 mmol), 3-(methylsulfonyl)aniline (182 mg, 1.07 mmol) and DIEA (375 g, 2.91 mmol) in 20 mL of DMSO was stirred at room temperature overnight. The mixture was poured into 150 mL of water and filtered, the solid obtained was washed with petroleum ether dried to give crude product which was purified by silica gel chromatography, silica gel 200-300 mesh, eluting with ethyl acetate to give 5-chloro-N-(3-(methylsulfonyl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine (220 mg, 66%) as a yellow solid. LC-MS: 341 [M+H]+, 3621 [M+Na]+, tR=1.48 min.

Aufarbeitung

  1. filtrationfiltered
  2. customthe solid obtained
  3. washwas washed with petroleum ether
  4. customdried
  5. customto give crude product which
  6. customwas purified by silica gel chromatography, silica gel 200-300 mesh
  7. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-e2a1636c09e24f2db36d3015fdf41f92
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921383B2

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