HCID 68781024, compound → HCID 68781256, compound

HRID 2264427Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:20]=[CH:19][C:18](Br)=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cu][C:23]#[N:24]>CC(N(C)C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:20]=[CH:19][C:18]([C:23]#[N:24])=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 4-(5-bromo-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (1.00 g, 2.80 mmol, 1.0 equiv), copper(I) cyanide (0.38 g, 4.20 mmol, 1.5 equiv), tris(dibenzylideneacetone)dipalladium(0) (0.58 g, 0.56 mmol, 0.2 equiv) and 1,1′-bis(diphenylphosphino)ferrocene (0.31 g, 0.56 mmol, 0.2 equiv) in DMAc (8 mL) was heated by microwave irradiation to 180° C. for 30 min. The organic phase was concentrated under reduced pressure and the residue purified by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane/ethyl acetate providing 0.20 g (23%) of the title compound. MS (ISP): 304.4 [M+H]+.

Workup

concentrationThe organic phase was concentrated under reduced pressure
customthe residue purified by silica column chromatography
washeluting with a gradient of heptane/ethyl acetate providing 0.20 g (23%) of the title compound

Sources & evidence

ORD record: ord-87b25ac2fe964757a1d323411201d86f
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855194B2

Reaction notes

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