Ethyl Acetate → HCID 69102358, compound

HRID 2217226Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:17]#[N:18])=[N:4][C:5]([C:9]2[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)=[C:6](Cl)[N:7]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>O1CCOCC1.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>[NH2:1][C:2]1[C:3]([C:17]#[N:18])=[N:4][C:5]([C:9]2[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)=[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

3-Amino-5-chloro-6-(6-methoxy-3-pyridyl)-2-pyrazinecarbonitrile (1.35 g) was dissolved in dioxane (135 ml). To the solution were added phenylboronic acid (1.89 g) and Pd(PPh3)4 (179 mg) and Na2CO3 (2.19 g) in water (27 ml) at 25° C. The reaction mixture was heated at 80° C. for 2 hours, then at ambient temperature for 3 hours. The above mixture was portioned to EtOAc and water. The organic layer was separated and washed with aq. Na2CO3 and brine, and dried over MgSO4. Evaporation of solvent in vacuo gave oily residue, which was purified by chromatography on silica gel (EtOAc:n-Hexane=1:1, v/v) to give 3-amino-6-(6-methoxy-3-pyridyl)-5-phenyl-2-pyrazinecarbonitrile as yellow crystal which was crystallized from EtOAc (1.15 g).

Workup

customThe organic layer was separated
washwashed with aq. Na2CO3 and brine
dry with materialdried over MgSO4
customEvaporation of solvent in vacuo
customgave oily residue, which
customwas purified by chromatography on silica gel (EtOAc

Sources & evidence

ORD record: ord-a67437f9e25541f9a3c2e86daec93159
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07407961B2

Reaction notes

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