Sodium Hydroxide → HCID 22732442, compound

HRID 2084227Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:3]=1.[OH:18][C:19]1[CH:20]=[CH:21][C:22]([N+:26]([O-:28])=[O:27])=[C:23]([CH:25]=1)[NH2:24].[OH-].[Na+]>>[OH:18][C:19]1[CH:20]=[CH:21][C:22]([N+:26]([O-:28])=[O:27])=[C:23]([CH:25]=1)[NH:24][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:3]=1

Participants

Reactant 3

HCID 14798Sodium Hydroxide

HCID 1675273-Amino-4-nitrophenol

HCID 14859904-Chloro-2-(pyridin-3-yl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 22732442HCID 22732442, compoundYield 63.4%

Procedure

The title compound was prepared from 4-chloro-2-(3-pyridinyl)-6-trifluoromethylpyrimidine (60 mg, 0.23 mmol) and 5-hydroxy-2-nitroaniline (52 mg, 0.34 mmol) similar to Example 180. The reaction mixture was neutralized with 2N NaOH to pH 7.0 and the solvent was removed under vacuo. The product was purified by column chromatography (20% ethyl acetate in hexane) to give 55 mg (63%) of the title compound as a light yellow solid. 1H NMR (CDCl3): 9.40 (d, J=1.2 Hz, 1H), 8.71 (dd, J=1.2, 4.8 Hz, 1H), 8.57(ddd, J=2.1, 3.9, 7.8 Hz, 1H), 8.04 (d, J=2.7 Hz, 1H), 7.42 (dd, J=3.9, 8.7 Hz, 1H), 7.32 (dd, J=6.0, 9.0 Hz, 1H), 7.23 (s, 1H), 6.92 (d, J=9.0 Hz, 1H), 6.19 (s, 2H).

Workup

customthe solvent was removed under vacuo
customThe product was purified by column chromatography (20% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-14e8c8807dad480f96bbd3523532850c
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06716851B2

Reaction notes

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