Nitrogen → 4-(2-Amino-6-{[(2-chlorophenyl)methyl]amino}-4-pyrimidinyl)-2-fluorobenzonitrile

HRID 2367244Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 6-chloro-N4-[(2-chlorophenyl)methyl]-2,4-pyrimidinediamine (1.2 g, 4.46 mmol) and 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (1.32 g, 5.35 mmol) in 1,4-dioxane (14.6 mL) and a solution of NaHCO3 (3.12 mmol) in water (20 mL) was protected with N2. Pd(Ph3P)4 (100 mg, 0.087 mmol) was added, and the reaction mixture was heated at 100° C. for 16 hours. The mixture was decanted to remove the solids, and the resulting solution was concentrated to dryness. The crude material was purified by SiO2 chromatography (1:2 THF:petroleum ether) to afford the title compound (800 mg) as a yellow solid. LC-MS (ES) m/z=354 [M+H]+.

Workup

customThe mixture was decanted
customto remove the solids
concentrationthe resulting solution was concentrated to dryness
customThe crude material was purified by SiO2 chromatography (1:2 THF:petroleum ether)

Sources & evidence

ORD record: ord-eb7846232b654582a2dbbe2002e08029
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

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