Diisopropylethylamine → HCID 86613131, Verbindung

HRID 60527

Reaktionsgleichung

[CH2:1]([S:8][C:9]1[N:10]=[C:11](Cl)[C:12]2[S:17][C:16]([NH2:18])=[N:15][C:13]=2[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH3:29][NH:30][C@@H:31]([CH2:36][OH:37])[CH2:32][CH:33]([CH3:35])[CH3:34]>CN1C(=O)CCC1>[NH2:18][C:16]1[S:17][C:12]2[C:11]([N:30]([CH3:29])[C@H:31]([CH2:32][CH:33]([CH3:35])[CH3:34])[CH2:36][OH:37])=[N:10][C:9]([S:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:14][C:13]=2[N:15]=1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

5-(Benzylthio)-7-chloro[1,3]thiazolo[4,5-d]pyrimidin-2-amine (1.5 g, 4.86 mmol), DIPEA (691 mg, 5.35 mmol) and (R)—N-methylleucinol (956 mg, 7.29 mmol) were mixed in NMP (7.5 mL). The resulting solution was stirred at 110° C. under a nitrogen atmosphere for 2 days. After cooling to room temperature the reaction mixture was poured onto ice. The resulting yellow precipitate was collected by filtration, washed with water and dried in vacuo. The crude product was purified by flash column chromatography on silica (DCM:EtOAc 50:50 to 0:100) to give 1.42 g (72% yield) of the title compound as a yellow solid.

Aufarbeitung

temperatureAfter cooling to room temperature the reaction mixture
additionwas poured onto ice
filtrationThe resulting yellow precipitate was collected by filtration
washwashed with water
customdried in vacuo
customThe crude product was purified by flash column chromatography on silica (DCM:EtOAc 50:50 to 0:100)

Quellen und Nachweise

ORD-Eintrag: ord-f0a8b299aa924c8facecfbf85b09942e
Quelldatensatz: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09440992B2

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