Sodium Bicarbonate → (R)-Methyl 2-((2-chloro-5-nitropyrimidin-4-yl)(cyclopentyl)amino)butanoate

HRID 2364663Notes

Reaction equation

[CH:1]1([NH:6][C@H:7]([CH2:12][CH3:13])[C:8]([O:10][CH3:11])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].[Cl:19][C:20]1[N:25]=[C:24](Cl)[C:23]([N+:27]([O-:29])=[O:28])=[CH:22][N:21]=1>C1CCCCC1>[Cl:19][C:20]1[N:25]=[C:24]([N:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[C@H:7]([CH2:12][CH3:13])[C:8]([O:10][CH3:11])=[O:9])[C:23]([N+:27]([O-:29])=[O:28])=[CH:22][N:21]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Methyl (2R)-2-(cyclopentylamino)butanoate 1k (2.50 g, 13.50 mmol) and sodium bicarbonate (4.54 g, 54 mmol) were dissolved in 100 mL of cyclohexane, stirred for 30 minutes followed by the addition of 2,4-dichloro-5-nitro-pyrimidine (2.88 g, 14.84 mmol), heated to 60° C. and stirred for another 12 hours. The reaction mixture was filtered, washed with dichloromethane (50 mL), and the filtrate was concentrated under reduced pressure, the resulting residue was recrystallized by 150 mL of the mixture solvent of ethyl acetate and n-hexane (V/V=1:4) to obtain the title compound methyl (2R)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-(1-cyclopentyl)amino]butanoate 1m (3.36 g, yield: 72.6%) as a light yellow solid.

Workup

stirringstirred for another 12 hours
filtrationThe reaction mixture was filtered
washwashed with dichloromethane (50 mL)
concentrationthe filtrate was concentrated under reduced pressure
customthe resulting residue was recrystallized by 150 mL of the mixture solvent of ethyl acetate and n-hexane (V/V=1:4)

Sources & evidence

ORD record: ord-ab0765c4c4ee474aa0f12a5b24397d9d
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691822B2

Reaction notes

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