Sodium Carbonate → HCID 118103325, compound

HRID 2207367Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[N:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][N:19]=2)[CH:5]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:7]=1.I[C:29]1[CH:30]=[CH:31][C:32]([NH2:35])=[N:33][CH:34]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:35][C:32]1[N:33]=[CH:34][C:29]([C:6]2[CH:5]=[C:4]([NH:17][C:18]3[N:23]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:21]=[CH:20][N:19]=3)[CH:3]=[C:2]([CH3:1])[CH:7]=2)=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of N-[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (1.29 g, 3.41 mmol), 5-iodopyridin-2-amine (500 mg, 2.27 mmol), PdCl2(dppf) (333 mg, 0.455 mmol) and sodium carbonate (2.27 ml, 4.55 mmol) in dioxane (9.10 mL) was heated to 100° C. for 16 hours. The reaction mixture was then filtered through a CELITE plug and washed with 1:1 DCM:methanol. The residue was purified by silica gel chromatography (ethyl acetate/hexanes) to give N-[3-(6-aminopyridin-3-yl)-5-methylphenyl]-4-(trifluoromethyl)pyrimidin-2-amine as a colorless solid. MS APCI calc'd for C17H15F3N5 [M+H]+ 346. found 346.

Workup

filtrationThe reaction mixture was then filtered through a CELITE plug
washwashed with 1:1 DCM
customThe residue was purified by silica gel chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-eaa8c7e21197425c8647d1e100d190a5
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376418B2

Reaction notes

Loading…