p-Toluidine → HCID 11243177, compound

HRID 1244766Notes

Reaction equation

HRID 1244766 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[C:4]([Cl:10])=[N:5][C:6](Cl)=[N:7][CH:8]=1.[CH3:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.C(N(CC)CC)C>CCOCC.ClCCCl.CC(O)(C)C.[Cl-].[Zn+2].[Cl-]>[Cl:10][C:4]1[C:3]([C:2]([F:12])([F:11])[F:1])=[CH:8][N:7]=[C:6]([NH:18][C:17]2[CH:19]=[CH:20][C:14]([CH3:13])=[CH:15][CH:16]=2)[N:5]=1

Participants

7

Reactant 3

HCID 7813p-ToluidineHCID 8471TriethylamineHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidine

Product 1

HCID 11243177HCID 11243177, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolventHCID 21868497Tert-butyl alcohol 1,2-dichloroethaneSolvent2×

Procedure

To a solution of 5-trifluoromethyl-2,4-dichloropyrimidine (2 g; 9.2 mmol) in 1:1 DCE/t-BuOH (80 mL) was added Zinc chloride (11 mL of a 1M solution in ether; 1.2 eq) at 0° C. After 1 hour, 4-methylaniline (988 mg; 1 eq) was added followed by dropwise addition of a solution of triethylamine (1.03 g; 1.1 eq) in 10 mL of DCE/t-BuOH. After stirring for 1.5 hours the reaction was concentrated. Analytical HPLC analysis revealed that the crude reaction contained <5% of isomer 9. The desired product 8 was obtained as a white solid (2.25 g; 85%) following crystallization from methanol. HPLC ret. Time: 8.169 min. LRMS (M+): 288.2, 290.1.

Workup

  1. customat 0° C
  2. concentrationwas concentrated
  3. customreaction

Sources & evidence

ORD record
ord-9137cfa93be64fe697f8d19f8991f811
Source dataset
uspto-grants-2006_10
Patent number
US07122670B2

Reaction notes

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