4-Chloroaniline → (4-Chloro-phenyl)-(2-chloro-6-trifluoromethyl-pyrimidin-4-yl)-amine

HRID 241345Notes

Reaction equation

HRID 241345 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1.CCN(C(C)C)C(C)C>C(O)CCC>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:6]2[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=[C:2]([Cl:1])[N:7]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 81531DiisopropylethylamineHCID 3342032,4-Dichloro-6-(trifluoromethyl)pyrimidine

Product 1

HCID 58451036(4-Chloro-phenyl)-(2-chloro-6-trifluoromethyl-pyrimidin-4-yl)-amine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2,4-dichloro-6-trifluoromethyl-pyrimidine (90 mg, 0.41 mmol) in n-butanol (1 mL), was added 4-chloro-phenylamine (52 mg, 0.416 mmol) and DIPEA (72 uL, 0.416). The mixture was stirred at 100° C. for overnight. The LC-MS showed the desired product mass [MS:(ESI), M/Z, 308 (M+1). Retention time: 2.70 min (FA-polar)]. This intermediate was used in situ without purification.

Sources & evidence

ORD record
ord-1935d4bdef384d1fb76adc5f9cb5b3d2
Source dataset
uspto-grants-2014_02
Patent number
US08648197B2

Reaction notes

Loading…