Ethyl Acetate → HCID 58504625, compound

HRID 2367214Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([F:16])[CH:9]=2)[CH:5]=[C:4](Cl)[N:3]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>O1CCOCC1.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[N:7]=[C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([F:16])[CH:9]=2)[CH:5]=[C:4]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[O:19][CH3:18])[N:3]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 4-(2-amino-6-chloro-4-pyrimidinyl)-2-fluorobenzonitrile (298 mg, 1.2 mmol), [2-(methyloxy)phenyl]boronic acid (273 mg, 1.8 mmol) and Na2CO3 (318 mg in 2 mL of water) in 1,4-dioxane (8 mL), was degassed with N2. Pd(PPh3)4 (69 mg, 0.06 mmol) was added, and the reaction mixture was stirred overnight at 95° C. The reaction was poured onto water and EtOAc. The organic layer was separated, and the aqueous layer was further extracted with EtOAc (2×). The combined organic layers were dried (MgSO4), filtered and concentrated to afford the crude title compound (306 mg). LC-MS (ES) m/z=321 [M+H]+.

Workup

customwas degassed with N2
customThe organic layer was separated
extractionthe aqueous layer was further extracted with EtOAc (2×)
dry with materialThe combined organic layers were dried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-82cc2a4e8b9540168eab1a327024f003
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

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