Sodium Hydroxide → Ethyl 2-(4-(4-chloropyrimidin-2-ylamino)-1h-pyrazol-1-yl)-2-methylpropanoate

HRID 714896Notes

Reaction equation

[CH3:1][C:2]([N:9]1[CH:13]=[C:12]([NH:14][C:15]2[NH:16][C:17](=O)[CH:18]=[CH:19][N:20]=2)[CH:11]=[N:10]1)([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].P(Cl)(Cl)([Cl:24])=O.[OH-].[Na+]>C(#N)C>[Cl:24][C:17]1[CH:18]=[CH:19][N:20]=[C:15]([NH:14][C:12]2[CH:11]=[N:10][N:9]([C:2]([CH3:8])([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:13]=2)[N:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 2-methyl-2-(4-((6-oxo-1,6-dihydropyrimidin-2-yl)amino)-1H-pyrazol-1-yl)propanoate (2.0 g) obtained in Step C of Example 347 in acetonitrile (20 mL) was added phosphorus oxychloride (4.0 mL), and the mixture was stirred at 80° C. for 2 hr. To the reaction mixture was added 8 M aqueous sodium hydroxide solution (25 mL), and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (2.0 g).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe obtained organic layer was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-a7a482fc58344a68aec81e8e5b8b5483
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187453B2

Reaction notes

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