Diisopropylethylamine → N-(3-((1R,5S)-8-oxa-3-azabicyclo[3.2.1]octan-3-yl)phenyl)-5-chlorothiazolo[5,4-d]pyrimidin-7-amine

HRID 1410067

Reaction equation

[C@@H:1]12[O:8][C@@H:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12])[CH2:2]2.[Cl:16][C:17]1[N:18]=[C:19](Cl)[C:20]2[N:25]=[CH:24][S:23][C:21]=2[N:22]=1.CCN(C(C)C)C(C)C>CS(C)=O.O>[C@@H:1]12[O:8][C@@H:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[CH:10]=[C:11]([NH:12][C:19]3[C:20]4[N:25]=[CH:24][S:23][C:21]=4[N:22]=[C:17]([Cl:16])[N:18]=3)[CH:13]=[CH:14][CH:15]=1)[CH2:2]2

Participants

Conditions

Temperature: 30 °C

Procedure

The mixture of 3-((1R,5S)-8-oxa-3-azabicyclo[3.2.1]octan-3-yl)aniline (0.061 g, 0.3 mmol), 5,7-dichlorothiazolo[5,4-d]pyrimidine (0.061 g, 0.3 mmol) and DIPEA (0.046 g, 0.36 mmol) in DMSO (10 mL) was heated to 30° C. for 2 h. Then it was diluted with water and extracted with ethyl acetate (3×10 mL), the organics were dried and concentrated. The residue was purified by column chromatography (silica gel, 200˜300 mesh, eluting with MeOH:DCM=1:80) to afford N-(3-((1R,5S)-8-oxa-3-azabicyclo[3.2.1]octan-3-yl)phenyl)-5-chlorothiazolo[5,4-d]pyrimidin-7-amine (0.095 g, 86%) as a yellow solid. LC-MS: 374 [M+H]+, tR=1.66 min.

Workup

extractionextracted with ethyl acetate (3×10 mL)
customthe organics were dried
concentrationconcentrated
customThe residue was purified by column chromatography (silica gel, 200˜300 mesh, eluting with MeOH:DCM=1:80)

Sources & evidence

ORD record: ord-26f0d20983bd490c9364c0ed844e1b01
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921383B2

Linked notes

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