Water → 1-[3-((E)-2-cyclohexylvinyl)pyrido[2,3-b]pyrazin-6-yl]-3-ethylurea

HRID 1511819Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]2[N:8]=[C:9]([NH:12][C:13]([NH:15][CH2:16][CH3:17])=[O:14])[CH:10]=[CH:11][C:5]2=[N:4][CH:3]=1.[CH:18]1([CH:24]=[CH:25]B(O)O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:18]1(/[CH:24]=[CH:25]/[C:2]2[N:7]=[C:6]3[N:8]=[C:9]([NH:12][C:13]([NH:15][CH2:16][CH3:17])=[O:14])[CH:10]=[CH:11][C:5]3=[N:4][CH:3]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

Conditions

Temperature: 90 °C

Procedure

99.6 mg of 1-(3-chloropyrido[2,3-b]pyrazin-6-yl)-3-ethylurea (0.40 mmol), 73.6 mg of cyclohexylvinylboronic acid (0.48 mmol), 84.4 mg of sodium carbonate (0.80 mmol) and 33.4 mg of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.04 mmol) were initially charged in 6 ml of dimethylformamide/water (1:1) under nitrogen. The mixture was then heated to 90° C. for 6.5 h. Distilled water was then added to the reaction mixture and the resulting precipitate was filtered off with suction. The further purification was effected by column chromatography on silica gel (ethyl acetate/heptane eluent mixture). A light brown solid was obtained.

Workup

filtrationthe resulting precipitate was filtered off with suction
customThe further purification
customA light brown solid was obtained

Sources & evidence

ORD record: ord-bb836e82f9204d52b9a74b7116952c80
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217042B2

Reaction notes

Loading…