Acetonitrile → HCID 178509577, compound

HRID 2367531Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH:10]([C:14]3[NH:15][CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[Cl:25])[N:18]=3)[CH2:9]2)[N:5]=[C:4]([NH2:26])[N:3]=1.[F:27][C:28]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[CH:32][C:29]=1[C:30]#[N:31].C([O-])([O-])=O.[Na+].[Na+].CC#N>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>[NH2:26][C:4]1[N:3]=[C:2]([C:34]2[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[C:28]([F:27])[CH:35]=2)[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH:10]([C:14]3[NH:15][CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[Cl:25])[N:18]=3)[CH2:9]2)[N:5]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 4-chloro-6-{2-[4-(2-chlorophenyl)-1H-imidazol-2-yl]-4-morpholinyl}-2-pyrimidinamine (100 mg, 0.256 mmol), 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (82 mg, 0.332 mmol), Na2CO3 (67.7 mg, 0.639 mmol) and Pd(PPh3)4 (29.5 mg, 0.026 mmol) in 1,4-dioxane (4 mL) and water (1 mL) was heated at 140° C. under microwave conditions with stirring for 1 hour. The reaction mixture was filtered, washed by EtOAc (100 mL), and concentrated. The resulting residue was purified by prep-HPLC using CH3CN in water (10 mmol NH4HCO3 in water) from 60% to 70% in 7 minutes to afford the title compound (50 mg) as a yellow solid. LC-MS (ES) m/z=476 [M+H]+.

Workup

filtrationThe reaction mixture was filtered
washwashed by EtOAc (100 mL)
concentrationconcentrated
customThe resulting residue was purified
customin 7 minutes

Sources & evidence

ORD record: ord-29b5ec7a8da7425b8b999bf58f17b5fb
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

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