Potassium Carbonate → HCID 118483179, compound

HRID 1773338Notes

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

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of tert-butyl 1-(5-chloro-4-(4-cyanophenyl)-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)piperidin-4-ylcarbamate (200 mg, 0.45 mmol), p-tolylboronic acid (123 mg, 0.90 mmol), [1,1′-bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) (28 mg, 0.045 mol) and K2CO3 (124 mg, 0.90 mmol) in DMF (10 mL) was flushed with nitrogen and stirred at 85° C. for 2 h. Water was added, and the mixture was extracted with EA (3×). The organics were combined, washed with water, washed with brine, dried and concentrated in vacuo. The residue was purified by silica chromatography (1:1, EA:PE) to give 50 mg (22%) of the title compound. [M+H] Calc'd for C29H33N5O3, 500. Found, 500.

Workup

customwas flushed with nitrogen
additionWater was added
extractionthe mixture was extracted with EA (3×)
washwashed with water
washwashed with brine
customdried
concentrationconcentrated in vacuo
customThe residue was purified by silica chromatography (1:1, EA:PE)

Sources & evidence

ORD record: ord-0c616f3870c14610804a4da0631f7238
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255097B2

Reaction notes

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