4-Chloro-2-(trifluoromethyl)pyrimidine → HCID 10427340, compound

HRID 1765099Notes

Reaction equation

HRID 1765099 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[N:8]=[C:7](Cl)[CH:6]=[CH:5][N:4]=1.[F:12][C:13]1[C:14]2[N:15]([C:30]([Sn](CCCC)(CCCC)CCCC)=[CH:31][N:32]=2)[CH:16]=[CH:17][C:18]=1[C:19]([O:22][Si](CC)(CC)CC)([CH3:21])[CH3:20]>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.C1COCC1>[F:12][C:13]1[C:14]2[N:15]([C:30]([C:7]3[CH:6]=[CH:5][N:4]=[C:3]([C:2]([F:11])([F:10])[F:1])[N:8]=3)=[CH:31][N:32]=2)[CH:16]=[CH:17][C:18]=1[C:19]([OH:22])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 152943694-Chloro-2-(trifluoromethyl)pyrimidineHCID 69549769HCID 69549769, compound

Product 1

HCID 10427340HCID 10427340, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Trifluoromethyl-4-chloropyrimidine (100 mg, 0.55 mmol) and tetrakis(triphenylphosphine)palladium(0) (25 mg, 0.022 mmol) were combined with a THF solution of 8-fluoro-3-(tri-n-butylstannyl)-7-[2-(triethylsilyloxy)prop-2-yl]imidazo[1,2-α]pyridine (circa 0.2 M; 3 ml, circa 0.6 mmol) and heated to reflux, with stirring, for 3 h. After cooling, the solution was concentrated onto silica and purified by column chromatography (silica; 50% EtOAc/isohexane), then the silyl protection removed by treatment with an ethanolic solution of 37% hydrochloric acid (5 drops in 2 ml of ethanol), affording the title compound as a white amorphous solid: δH (360 MHz, CDCl3) 1.77 (6H, s), 7.48 (1H, m), 7.78 (1H, d, J 5.6), 8.42 (1H, s), 9.42 (1H, m), 9.71 (1H, d, J 7.6); m/z (ES+) 341 (100%, [MH]+).

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. temperatureAfter cooling
  4. concentrationthe solution was concentrated onto silica
  5. custompurified by column chromatography (silica; 50% EtOAc/isohexane)
  6. customthe silyl protection removed by treatment with an ethanolic solution of 37% hydrochloric acid (5 drops in 2 ml of ethanol)

Sources & evidence

ORD record
ord-683d1b73e45849bb90fbbd35c65d92e0
Source dataset
uspto-grants-2007_06
Patent number
US07226926B2

Reaction notes

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