Sodium Carbonate → HCID 118483133, compound

HRID 1773341Notes

Reaction equation

[C:1]([O:5][C:6](=[O:24])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]([CH2:22][CH3:23])[C:16](=[O:21])[CH:17]=[C:18](Cl)[N:19]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[F:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][C:31]=1[C:32]#[N:33].C([O-])([O-])=O.[Na+].[Na+]>CC#N>[C:1]([O:5][C:6](=[O:24])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]([CH2:22][CH3:23])[C:16](=[O:21])[CH:17]=[C:18]([C:28]3[CH:29]=[CH:30][C:31]([C:32]#[N:33])=[C:26]([F:25])[CH:27]=3)[N:19]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of [1-(4-chloro-1-ethyl-6-oxo-1,6-dihydro-pyrimidin-2-yl)-piperidin-4-yl]-carbamic acid tert-butyl ester (210 mg, 0.59 mmol) in CH3CN (10 mL), 3-fluoro-4-cyanophenylboronic acid (126 mg, 0.77 mmol), Pd(PPh)4 (14 mg, 0.012 mmol) and 0.4 M Na2CO3 (4.5 mL, 1.77 mmol) was stirred at 90° C. overnight under N2 atmosphere. The organic was concentrated in vacuo, and the aqueous extracted with DCM (2×). The combined organics were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by silica chromatography (1:2, EA:PE) to give 185 mg (64%) of the title compound as a yellow solid. [M+H] Calc'd for C23H28FN5O3, 442. Found, 442.

Workup

concentrationThe organic was concentrated in vacuo
extractionthe aqueous extracted with DCM (2×)
washThe combined organics were washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe residue was purified by silica chromatography (1:2, EA:PE)

Sources & evidence

ORD record: ord-53286e3e7774493e8e23c902dca3e0a9
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255097B2

Reaction notes

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