Triphenylarsine → 4-Chloro-2-(6-chloropyrimidin-4-yl)aniline

HRID 1408122Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:3]=1.[Cl:18][C:19]1[CH:24]=[C:23](Cl)[N:22]=[CH:21][N:20]=1.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([C:23]2[CH:24]=[C:19]([Cl:18])[N:20]=[CH:21][N:22]=2)[CH:3]=1

Participants

Conditions

Temperature: 75 °C

Procedure

Into a 250-mL round bottom flask, was placed a solution of 4-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine (3 g, 11.83 mmol, 1.00 equiv) in dioxane (120 mL), water (20 mL), 4,6-dichloropyrimidine (4.4 g, 29.53 mmol, 2.50 equiv), triphenylarsine (360 mg, 1.18 mmol, 0.10 equiv), K3PO4 (3.8 g, 17.90 mmol, 1.50 equiv), Pd(PPh3)2Cl2 (390 mg, 0.56 mmol, 0.05 equiv). The resulting solution was stirred for 3 h at 75° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:50˜1:10). This resulted in 1.5 g (53%) of 4-chloro-2-(6-chloropyrimidin-4-yl)benzenamine as a yellow solid.

Workup

customInto a 250-mL round bottom flask, was placed
concentrationThe resulting mixture was concentrated under vacuum
customThis resulted in 1.5 g (53%) of 4-chloro-2-(6-chloropyrimidin-4-yl)benzenamine as a yellow solid

Sources & evidence

ORD record: ord-ee65555f6c72487cac45db9111278dab
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916569B2

Reaction notes

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