Triethylamine → 2-[4-(6-fluorobenzo[b]thiophen-3-yl)piperidin-1-yl]-1-methyl-1H-[4,4']bipyrimidinyl-6-one

HRID 1784724Notes

Reaction equation

Cl.[F:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[CH:9][S:8][C:7]=2[CH:17]=1.Cl[C:19]1[N:20]([CH3:32])[C:21](=[O:31])[CH:22]=[C:23]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][N:26]=2)[N:24]=1.C(N(CC)CC)C>O1CCCC1>[F:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([CH:11]3[CH2:12][CH2:13][N:14]([C:19]4[N:20]([CH3:32])[C:21](=[O:31])[CH:22]=[C:23]([C:25]5[CH:30]=[CH:29][N:28]=[CH:27][N:26]=5)[N:24]=4)[CH2:15][CH2:16]3)=[CH:9][S:8][C:7]=2[CH:17]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 4-(6-fluorobenzo[b]thiophen-3-yl)piperidine hydrochloride (200 mg, 0.74 mmol) and 2-chloro-1-methyl-1H-[4,4′]bipyrimidinyl-6-one (160 mg, 0.70 mmol) in tetrahydrofuran (10 mL) was added triethylamine (212 mg, 2.1 mmol). The mixture was stirred at 90° C. for 6 h. The solvent was evaporated off in vacuo and the residue was treated with water and chloroform. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. Recrystallization from ethyl acetate gave 2-[4-(6-fluorobenzo[b]thiophen-3-yl)piperidin-1-yl]-1-methyl-1H-[4,4′]bipyrimidinyl-6-one (220 mg, 96%) as colorless crystals.

Workup

customThe solvent was evaporated off in vacuo
additionthe residue was treated with water and chloroform
dry with materialThe organic layer was dried over sodium sulfate
customthe solvent was evaporated under reduced pressure
customRecrystallization from ethyl acetate

Sources & evidence

ORD record: ord-eca6b135471b4a8f969414b2b1546cd5
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504411B2

Reaction notes

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