Methanol → HCID 90402691, compound

HRID 718187Notes

Reaction equation

[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)=[C:6]([CH3:21])[CH:5]=[C:4]([N+:22]([O-])=O)[N:3]=1.[NH4+].[Cl-].CO.C1COCC1>[Zn].CCOC(C)=O>[CH3:21][C:6]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)=[C:2]([CH3:1])[N:3]=[C:4]([NH2:22])[CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2,4-Dimethyl-3-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)-6-nitropyridine (0.56 g, 1.8 mmol) and NH4Cl (2.76 g, 51.6 mmol) were combined in a solution of MeOH (8.6 mL) and THF (8.6 mL) and cooled to 0° C. Zinc powder (1.13 g, 17.2 mmol) was added portion-wise over 30 min and the reaction mixture was allowed to warm to RT and stirred vigorously for 12 h. EtOAc (100 mL) was added and the resultant suspension was filtered through a pad of diatomaceous earth. The filter cake was washed with EtOAc (3×10 mL) and the combined filtrates were concentrated in vacuo. The residue was purified by silica gel chromatography (MeOH/DCM) to afford 4,6-dimethyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-amine (0.41 g, 81%) as a light red solid. MS (ESI) m/z: 296.1 (M+H+).

Workup

temperatureto warm to RT
filtrationthe resultant suspension was filtered through a pad of diatomaceous earth
washThe filter cake was washed with EtOAc (3×10 mL)
concentrationthe combined filtrates were concentrated in vacuo
customThe residue was purified by silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record: ord-b96d52c011b14a2ca4866bcce8471614
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193719B2

Reaction notes

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