Hydrochloric Acid → 5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyrazin-2-amine

HRID 1049277Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of N-(5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyrazin-2-yl)acetamide (0.38 g, 1.22 mmol) in THF (10 mL) was treated with aqueous HCl (2 M, 6.12 mL, 12.24 mmol) and the solution was stirred at 60° C. for 4 h. The solvent was evaporated and the crude residue was diluted with water (40 mL), basified with solid NaHCO3, and extracted with EtOAc (2×30 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated to afford 5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyrazin-2-amine (0.32 g, 97%) as a white foam. 1H NMR (400 MHz, DMSO-d6): δ 8.34 (d, J=5.7 Hz, 1H), 8.25 (s, 1H), 7.95 (d, J=0.7 Hz, 1H), 7.91 (d, J=1.4 Hz, 1H), 7.61 (d, J=1.4 Hz, 1H), 7.21 (d, J=2.4 Hz, 1H), 6.69 (dd, J=5.7, 2.4 Hz, 1H), 6.44 (s, 2H), 3.84 (s, 3H); MS (ESI) m/z: 269.1 (M+H+).

Workup

customThe solvent was evaporated
additionthe crude residue was diluted with water (40 mL)
extractionextracted with EtOAc (2×30 mL)
washThe combined organics were washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-9cfd61a7b51f4fa2badb2c7b4123f7bb
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382228B2

Reaction notes

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