Ammonium Hydroxide → 7-Bromo-4-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-1-yl]-thieno[3,2-d]pyrimidine

HRID 532474

Reaction equation

[Br:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10](Cl)[C:5]=2[S:4][CH:3]=1.[CH:12]([C:15]1[N:19]=[C:18]([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[O:17][N:16]=1)([CH3:14])[CH3:13].C(N(C(C)C)CC)(C)C.[OH-].[NH4+]>C(O)(C)C>[Br:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([N:23]3[CH2:22][CH2:21][CH:20]([C:18]4[O:17][N:16]=[C:15]([CH:12]([CH3:14])[CH3:13])[N:19]=4)[CH2:25][CH2:24]3)[C:5]=2[S:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

7-bromo-4-chlorothieno[3,2-d]pyrimidine (100 mg) was added to isopropyl alcohol (3 mL), and 4-(3-isopropyl-[1,2,4]-oxadiazol-5-yl)piperidine (100 mg) and diisopropylethylamine (200 μL) were further added thereto. The reaction mixture was stirred at 100° C. for 12 hours. Then, the reaction mixture was mixed with saturated ammonium hydroxide solution and extracted twice with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a foamy residue. The residue was crystallized in the presence of diethyl ether to obtain the title compound (100 mg) as a whitish solid.

Workup

additionwere further added
extractionextracted twice with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customto obtain a foamy residue
customThe residue was crystallized in the presence of diethyl ether

Sources & evidence

ORD record: ord-5eb4980247e24944baaa66c8fdd70aa6
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853213B2

Linked notes

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