Triethylamine → HCID 57877729, compound

HRID 1091407Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][CH2:11][NH:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[C:15]1[N:20]([CH3:21])[C:19](=[O:22])[CH:18]=[C:17]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][C:24]=2[F:29])[N:16]=1.C(N(CC)CC)C>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:13][CH2:12][CH2:11][N:10]([C:15]3[N:20]([CH3:21])[C:19](=[O:22])[CH:18]=[C:17]([C:23]4[CH:28]=[CH:27][N:26]=[CH:25][C:24]=4[F:29])[N:16]=3)[CH2:9]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A solution of (3R)-3-(4-bromophenyl)piperidine obtained in Reference Example 15 (0.21 g, 0.9 mmol), 2-chloro-6-(3-fluoropyridin-4-yl)-3-methyl-3H-pyrimidine-4-one (0.21 g, 0.9 mmol), and triethylamine (0.30 g, 3.0 mmol) in tetrahydrofuran (10 ml) was stirred at 95° C. for 3 hours. The solvent was removed in vacuo and the residue was partitioned between water and dichloromethane. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform/methanol=10/1) to afford 2-((3R)-3-(4-bromophenyl)piperidin-1-yl)-6-(3-fluoropyridin-4-yl)-3-methyl-3H-pyrimidine-4-one (0.24 g, 62%) as colorless crystals.

Workup

customThe solvent was removed in vacuo
customthe residue was partitioned between water and dichloromethane
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customthe solvent was removed under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record: ord-a57fddf255594d33bcaeacfd61a0588c
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129377B2

Reaction notes

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