Water → Ethyl 2-(4-(1,6-dihydro-6-oxopyrimidin-2-ylamino)-1h-pyrazol-1-yl)-2-methylpropanoate

HRID 714895Notes

Reaction equation

CS[C:3]1[NH:8][C:7](=[O:9])[CH:6]=[CH:5][N:4]=1.[NH2:10][C:11]1[CH:12]=[N:13][N:14]([C:16]([CH3:23])([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:15]=1.O>COCCOCCOC>[CH3:23][C:16]([N:14]1[CH:15]=[C:11]([NH:10][C:3]2[NH:8][C:7](=[O:9])[CH:6]=[CH:5][N:4]=2)[CH:12]=[N:13]1)([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 2-(methylsulfanyl)pyrimidin-4(3H)-one (9.1 g) obtained in Step A of Example 347 in diglyme (60 mL) was added ethyl 2-(4-amino-1H-pyrazol-1-yl)-2-methylpropanoate (13 g) obtained in Step B of Example 347, and the mixture was stirred at 140° C. for 7 hr. To the reaction mixture was added water, 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. The residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give the title compound (17 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
customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record: ord-a9095934bae24788a865d81eb7711c60
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187453B2

Reaction notes

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