Potassium Carbonate → HCID 118483185, compound

HRID 1773343Notes

Reaction equation

Cl[C:2]1[C:7](=[O:8])[N:6]([CH3:9])[C:5]([N:10]2[CH2:15][CH2:14][CH:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:12][CH2:11]2)=[N:4][C:3]=1[C:24]1[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[C:26]([F:32])[CH:25]=1.[C:33]([CH:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1)#[CH:34].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[K+].[K+]>C(#N)C.CC#N.CC#N.Cl[Pd]Cl>[C:19]([O:18][C:17](=[O:23])[NH:16][CH:13]1[CH2:14][CH2:15][N:10]([C:5]2[N:6]([CH3:9])[C:7](=[O:8])[C:2]([C:34]#[C:33][CH:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)=[C:3]([C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[C:26]([F:32])[CH:25]=3)[N:4]=2)[CH2:11][CH2:12]1)([CH3:22])([CH3:21])[CH3:20]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of tert-butyl 1-(5-chloro-4-(3-fluoro-4-cyanophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)piperidin-4-ylcarbamate (200 mg, 0.43 mmol), ethynyl-cyclopentane (82 mg, 0.87 mmol), Pd(MeCN)2Cl2 (4.5 mg, 0.017 mmol), X-Phos (10 mg, 0.022 mmol) and K2CO3 (120 mg, 0.87 mmol) in ACN (15 mL) was stirred overnight at 95° C. in a sealed tube. The reaction mixture was cooled to RT and the solvent was concentrated in vacuo. The residue was purified by silica chromatography (1:2, EA:PE) to give 100 mg (45%) of the title compound. [M+H] Calc'd for C29H34FN5O3, 519. Found, 519.

Workup

temperatureThe reaction mixture was cooled to RT
concentrationthe solvent was concentrated in vacuo
customThe residue was purified by silica chromatography (1:2, EA:PE)

Sources & evidence

ORD record: ord-112905def4b040c1b7add9f42eaf91fb
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255097B2

Reaction notes

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