4-Bromoaniline → HCID 22346771, compound

HRID 898038Notes

Reaction equation

[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Cl[C:10]1[N:15]=[CH:14][CH:13]=[CH:12][N:11]=1>>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:10]2[N:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 78074-Bromoaniline

HCID 744042-Chloropyrimidine

Product 1

HCID 22346771HCID 22346771, compoundYield 31%

Procedure

4-Bromoaniline (0.300 g, 1.74 mmol) and 2-chloropyrimidine (0.200 g, 1.74 mmol) were heated neat at 150° C. in a 25 mL flask for 2 h. The reaction mixture was cooled to ambient temperature, and purification of the residue by preparative HPLC (25 to 100% acetonitrile in 0.1 M aqueous ammonium acetate over 20 min at 21 mL/min using an 8μ Hypersil HS C18, 250×21 mm column, Rt 13.8-15.9 min) afforded N-(4-bromophenyl)-N-(2-pyrimidinyl)amine as a yellow solid (0.135 g, 0.54 mmol); RP-HPLC (25 to 100% acetonitrile in 0.1 M aqueous ammonium acetate over 10 min at 1 mL/min using a 5μ Hypersil HS C18, 250×4.6 mm column) Rt 11.08 min; 1H NMR (DMSO-d6, 400 MHz) δ 9.78 (s, 1H), 8.50 (d, 2H), 7.76 (d, 2H), 7.45 (d, 2H), 6.87 (t, 1H).

Workup

custompurification of the residue by preparative HPLC (25 to 100% acetonitrile in 0.1 M aqueous ammonium acetate over 20 min at 21 mL/min

Sources & evidence

ORD record: ord-116ebee7db35493a837823d057b70f12
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921763B2

Reaction notes

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