Sodium Carbonate → 1-Ethyl-3-[3-(3-hydroxy-phenyl)-pyrido[2,3-b]pyrazine-6-yl]-urea

HRID 1428199Notes

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.CN(C)C=O.O.[OH:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH2:16]([NH:15][C:13]([NH:12][C:9]1[CH:10]=[CH:11][C:5]2[C:6]([N:8]=1)=[N:7][C:2]([C:29]1[CH:28]=[CH:27][CH:26]=[C:25]([OH:24])[CH:30]=1)=[CH:3][N:4]=2)=[O:14])[CH3:17]

Participants

Conditions

Temperature: 90 °C

Procedure

100 mg 1-(3-chloropyrido[2,3-b]pyrazine-6-yl)-3-ethyl-urea (0.40 mmol) was presented in a dimethylformamide/water mixture under nitrogen as protective gas. Then 60.3 mg 3-hydroxyphenyl boronic acid (0.44 mmol), 126 mg sodium carbonate (1.19 mmol) and 23 mg tetrakis(triphenylphosphine) palladium(0) (0.02 mmol) were added. The reaction mixture was stirred at 90° C. for 4 hours. The mixture was filled with water for reprocessing and the deposited solid rewashed with dichloromethane. The resulting raw product was stirred again in warm DCM, filtered off and dried. A yellow solid was obtained.

Workup

filtrationfiltered off
customdried
customA yellow solid was obtained

Sources & evidence

ORD record: ord-cb0db14be6bb48ee917625a45bc9980f
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937068B2

Reaction notes

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