Triethylamine → 4-[[2-(5-Bromo-2-fluorophenyl)pteridin-4-yl]amino]nicotinic Acid Methyl Ester

HRID 928265

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([C:8]2[N:17]=[C:16](Cl)[C:15]3[C:10](=[N:11][CH:12]=[CH:13][N:14]=3)[N:9]=2)[CH:7]=1.[CH3:20][O:21][C:22](=[O:30])[C:23]1[C:28]([NH2:29])=[CH:27][CH:26]=[N:25][CH:24]=1.C(N(CC)CC)C>ClC(Cl)C>[CH3:20][O:21][C:22](=[O:30])[C:23]1[C:28]([NH:29][C:16]2[C:15]3[C:10](=[N:11][CH:12]=[CH:13][N:14]=3)[N:9]=[C:8]([C:6]3[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=3[F:19])[N:17]=2)=[CH:27][CH:26]=[N:25][CH:24]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 2-(5-bromo-2-fluorophenyl)-4-chloropteridine 106 (200 mg, 0.589 mmol), 4-aminonicotinic acid methyl ester (224 mg, 1.47 mmol) in dichloroethane (5 mL), was added dropwise triethylamine (300 μL, 2.07 mmol). The resulting mixture was heated at 70° C. for 15 min, then quenched with silica and purified by column chromatography (AcOEt/CH2Cl2/triethylamine, 70/19/1). Crystallization from AcOEt/Et2O afforded 200 mg of the title product 107 as yellow prisms (LCMS analysis).

Workup

customquenched with silica
custompurified by column chromatography (AcOEt/CH2Cl2/triethylamine, 70/19/1)
customCrystallization from AcOEt/Et2O

Sources & evidence

ORD record: ord-9114b28750b041699f72acfb20787d81
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290502B2

Linked notes

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