Diisopropylethylamine → 5-bromo-N-(3-chloro-4-(difluoromethoxy)phenyl)pyrimidin-2-amine

HRID 77481Notes

Reaction equation

HRID 77481 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH:10]([F:12])[F:11])[NH2:5].CCN(C(C)C)C(C)C.Br[C:23]1[N:28]=[CH:27][C:26]([Br:29])=[CH:25][N:24]=1>C(O)CCC>[Br:29][C:26]1[CH:25]=[N:24][C:23]([NH:5][C:4]2[CH:6]=[CH:7][C:8]([O:9][CH:10]([F:11])[F:12])=[C:2]([Cl:1])[CH:3]=2)=[N:28][CH:27]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 20641533-Chloro-4-(difluoromethoxy)anilineHCID 109555882,5-Dibromopyrimidine

Product 1

HCID 866797715-bromo-N-(3-chloro-4-(difluoromethoxy)phenyl)pyrimidin-2-amineYield 64%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3-chloro-4-(difluoromethoxy)aniline (0.814 g, 4.20 mmol) in butan-1-ol (10 mL), were added DIPEA (2.203 mL, 12.61 mmol) and 2,5-dibromopyrimidine (1 g, 4.20 mmol). The reaction mixture was stirred at 120° C. for 12 h and concentrated. The crude product was purified by flash chromatography on silica gel using 3% ethyl acetate in petroleum ether to give 5-bromo-N-(3-chloro-4-(difluoromethoxy)phenyl)pyrimidin-2-amine (0.8 g, 64%). LCMS (ES-ES), m/z 349.98.

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by flash chromatography on silica gel using 3% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-d4fc892fab6f4730921e790bf0d273cb
Source dataset
uspto-grants-2014_09
Patent number
US08841301B2

Reaction notes

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