Sodium Carbonate → HCID 118483198, compound

HRID 1773352Notes

Reaction equation

[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]([CH2:22][CH2:23][CH2:24][OH:25])[C:16](=[O:21])[CH:17]=[C:18](Cl)[N:19]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:27]([C:29]1[CH:34]=[CH:33][C:32](OB(O)O)=[CH:31][C:30]=1[F:39])#[N:28].[C:40]([O-])([O-])=O.[Na+].[Na+]>C(#N)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]([CH2:22][CH2:23][CH2:24][O:25][CH3:40])[C:16](=[O:21])[CH:17]=[C:18]([C:32]3[CH:33]=[CH:34][C:29]([C:27]#[N:28])=[C:30]([F:39])[CH:31]=3)[N:19]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of {1-[4-chloro-1-(3-hydroxy-propyl)-6-oxo-1,6-dihydro-pyrimidin-2-yl]-piperidin-4-yl}-carbamic acid tert-butyl ester (200 mg, 0.5 mmol), 4-cyano-3-fluorophenyl boric acid (107 mg, 0.65 mmol), Pd(PPh3)4 (12 mg, 0.01 mmol) and 0.4M Na2CO3 solution (4 mL) in ACN was stirred at 85° C. overnight. The reaction mixture was diluted with water and extracted with EA (3×). The reaction mixture was stirred at RT for 2 h and the solvent was concentrated in vacuo. The residue was purified by silica chromatography to give 240 mg of the title product (99%). [M+H] Calc'd for C25H32FN5O4, 485. Found, 485.

Workup

extractionextracted with EA (3×)
stirringThe reaction mixture was stirred at RT for 2 h
concentrationthe solvent was concentrated in vacuo
customThe residue was purified by silica chromatography

Sources & evidence

ORD record: ord-3a8bb0da36494ffcab09e5c93c037e5a
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255097B2

Reaction notes

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