Sodium Carbonate → 3-Phenylpyrido[2,3-b]pyrazin-6-ylamine

HRID 1511822Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]2[N:8]=[C:9]([NH2:12])[CH:10]=[CH:11][C:5]2=[N:4][CH:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:13]1([C:2]2[N:7]=[C:6]3[N:8]=[C:9]([NH2:12])[CH:10]=[CH:11][C:5]3=[N:4][CH:3]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1.00 g of 3-chloropyrido[2,3-b]pyrazin-6-ylamine (5.54 mmol), 743 mg of phenylboronic acid (6.09 mmol), 640 mg of tetrakis(triphenylphosphine)palladium(0) (0.55 mmol) and 1.76 g of sodium carbonate (16.6 mmol) were initially charged in 100 ml of dimethylformamide/water (1:1) under nitrogen as a protective gas and stirred at 80° C. for 2 h. Once the reaction had ended, the mixture was filtered off with suction and the filtrate was poured onto 800 ml of distilled water. The aqueous phase was extracted repeatedly with ethyl acetate. The organic phase was freed of solvents under reduced pressure. The resulting solid was purified by means of column chromatography on silica gel (dichloromethane/methanol eluent). This gave a yellow solid.

Workup

filtrationthe mixture was filtered off with suction
additionthe filtrate was poured onto 800 ml of distilled water
extractionThe aqueous phase was extracted repeatedly with ethyl acetate
customThe resulting solid was purified by means of column chromatography on silica gel (dichloromethane/methanol eluent)
customThis gave a yellow solid

Sources & evidence

ORD record: ord-5fd82927a0c84e61a507af34532c933a
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217042B2

Reaction notes

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