Water → 3-chloro-4-fluoro-N-(5-nitropyrimidin-2-yl)benzamide

HRID 750474

Reaction equation

[N+:1]([C:4]1[CH:5]=[N:6][C:7]([NH2:10])=[N:8][CH:9]=1)([O-:3])=[O:2].[Cl:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[F:21])[C:15](O)=[O:16].O>N1C=CC=CC=1>[Cl:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[F:21])[C:15]([NH:10][C:7]1[N:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][N:6]=1)=[O:16]

Participants

Conditions

Temperature: 100 °C

Procedure

To 5-nitropyrimidin-2-amine (1.0 g, 7.1 mmol) in pyridine (10 mL) was added 3-chloro-4-fluorobenzoic acid (1.7 g, 9.7 mmol). The reaction mixture was heated at 100° C. for 4 hrs and allowed to cool to rt. 15 mL H2O was added. A precipitate was collected by filtration and purified by silica gel chromatography, eluting with CH2Cl2 followed by 10% EtOAc/CH2Cl2 to give 1.16 g (55% yield) 1C. RP HPLC ret. t.: 2.22 min. and (M+H)+: 297.

Workup

temperatureto cool to rt
filtrationA precipitate was collected by filtration
custompurified by silica gel chromatography
washeluting with CH2Cl2

Sources & evidence

ORD record: ord-24a01487731d47dc8b9d5a29cafbc925
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405213B2

Linked notes

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