Dimethylformamide → HCID 90041826, compound

HRID 929164Notes

Reaction equation

[CH2:1]1[C:4]2([CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5]2)[CH2:3][NH:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:22]1[N:27]=[CH:26][CH:25]=[CH:24][N:23]=1.CN(C=O)C>O.CCOC(C)=O>[N:23]1[CH:24]=[CH:25][CH:26]=[N:27][C:22]=1[N:2]1[CH2:3][C:4]2([CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5]2)[CH2:1]1

Participants

Conditions

Temperature: 102.5 °C

Procedure

A 2 L round-bottom flask was charged with tert-butyl 2,6-diazaspiro[3,3]heptane-6-carboxylate (64.3 g, 0.32 mol), cesium carbonate (317.0 g, 0.97 mol), 2-chloropyrimidine (45.5 g, 0.4 mol), and DMF (759.0 mL). The reaction mixture was heated to 100-105° C. for 20 min. The reaction mixture was cooled to ambient temperature, diluted with water (759.0 mL) and EtOAc (759.0 mL). The organic layer was washed with water (2×500.0 mL) and brine (500.0 mL). The organic layer was dried over sodium sulfate and filtered through Celite™. The filtrate was concentrated under reduced pressure. Column chromatography of the resulting crude product on silica gel, eluting with EtOAc and heptane (50-100%) afforded the desired product.

Workup

temperatureThe reaction mixture was cooled to ambient temperature
washThe organic layer was washed with water (2×500.0 mL) and brine (500.0 mL)
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered through Celite™
concentrationThe filtrate was concentrated under reduced pressure
washColumn chromatography of the resulting crude product on silica gel, eluting with EtOAc and heptane (50-100%)

Sources & evidence

ORD record: ord-d0988036922c4059a8433f31ca59e6df
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290517B2

Reaction notes

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