Sodium Carbonate → 2-Chloro-4-(4-(trifluoromethyl)phenyl)pyrimidine

HRID 1626467Notes

Reaction equation

HRID 1626467 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[Cl:14][C:15]1[N:20]=[C:19](Cl)[CH:18]=[CH:17][N:16]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:14][C:15]1[N:20]=[C:19]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=2)[CH:18]=[CH:17][N:16]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 775312,4-DichloropyrimidineHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 218652762-Chloro-4-(4-(trifluoromethyl)phenyl)pyrimidineYield 27.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

4-(trifluoromethyl)phenylboronic acid (319 mg, 1.68 mmol), 2,4-dichloropyrimidine (250 mg, 1.68 mmol), Na2CO3 (445 mg, 4.20 mmol) and Pd(PPh3)4 (97.0 mg, 0.0839 mmol) were combined in a 5 mL reaction vial and diluted with toluene (3 mL) and water (300 μL). The reaction was purged with argon, heated to 60° C. and stirred overnight. The reaction was loaded directly onto silica gel and eluted with 5% ethyl acetate/hexanes to 60% ethyl acetate/hexanes to yield the desired compound (120 mg, 0.464 mmol, 27.6% yield).

Workup

  1. customThe reaction was purged with argon
  2. washeluted with 5% ethyl acetate/hexanes to 60% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-43d4d11de6584cb5937cca6ec54bacc9
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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