Dichloromethane → methyl (2S)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]butanoate

HRID 2364755Notes

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.ClCCl>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: 85 °C

Procedure

Methyl (2S)-2-(cyclopentylamino)butanoate 41c (17.36 g, 93.69 mmol) was dissolved in 180 mL of cyclohexane followed by the addition of sodium bicarbonate (31.48 g, 0.37 mol) and 2,4-dichloro-5-nitro-pyrimidine (21.81 g, 0.11 mol) successively. The reaction solution was heated to 85° C. and stirred for 2 hours. The resulting solution was cooled down to room temperature, added with 300 mL of dichloromethane, then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography with elution system B to obtain the title compound methyl (2S)-2-[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclopentyl-amino]butanoate 41d (14.24 g, yield: 44.3%) as a yellow solid.

Workup

temperatureThe resulting solution was cooled down to room temperature
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationthe filtrate was concentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography with elution system B

Sources & evidence

ORD record: ord-7e44164c2db14dd5ab6b84a574757d33
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691822B2

Reaction notes

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