Tris(furan-2-yl)phosphane → HCID 86633386, compound

HRID 1475154Notes

Reaction equation

HRID 1475154 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[N:6]=[C:5]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[N:4]=1.FC(F)(F)C1C=C(C2C=CC([N+]([O-])=O)=CC=2)N=C(SC)N=1.[N+](C1C=CC(C(=O)CC(=O)C(F)(F)F)=CC=1)([O-])=O.FC(F)(F)C1C=CC(B(O)O)=CC=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>C1COCC1.S1C=CC=C1C([O-])=O.[Cu+2].S1C=CC=C1C([O-])=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[F:29][C:2]([F:1])([F:28])[C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[N:6]=[C:5]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:25])[F:26])=[CH:20][CH:19]=2)[N:4]=1

Participants

9

Reactant 5

HCID 521585Tris(furan-2-yl)phosphaneHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 110652044,4,4-trifluoro-1-(4-nitrophenyl)butane-1,3-dioneHCID 66968518HCID 66968518, compoundHCID 86633387HCID 86633387, compound

Product 1

HCID 86633386HCID 86633386, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 15171005Copper thiophene-2-carboxylateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
52 °C

Procedure

4-Trifluoromethyl-6-(4-nitrophenyl)-2-(4-trifluoromethyl-phenyl)-pyrimidine. A solution of 4-trifluoromethyl-2-methylsulfanyl-6-(4-nitrophenyl)-pyrimidine (1.25 g, 4.0 mmol, prepared from 1-(4-nitrophenyl-4,4,4-trifluorobutane-1,3-dione according to Green et al. WO 200138311 A2), 4-trifluoromethylphenylboronic acid (0.95 g, 5.0 mmol), trifurylphosphine (140 mg, 0.60 mmol), and copper (II) 2-thiophenecarboxylate (1.05 g, 5.0 mmol) were combined in 25 mL of dry THF and heated to 52° C. The catalyst tris(dibenzyl-ideneacetone)dipalladium(0)-chloroform adduct (100 mg) was then added in three portions over 3 h, and the solution was then allowed to stir at 50° C. for 12 h. Concentration and chromatography (Biotage, 4:1 hexane/DCM) furnished 0.67 g (41%) of the title compound as a light yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.75 (d, J=8 Hz, 2H), 8.41 (s, 4H), 8.03 (s, 1H), 7.80 (d, J=8 Hz, 2H); EIMS 414.1 (M+H); mp 162° C.

Workup

  1. concentrationConcentration and chromatography (Biotage, 4:1 hexane/DCM)

Sources & evidence

ORD record
ord-40167eeebec546d5b8b39150a0d1ede8
Source dataset
uspto-grants-2015_04
Patent number
US09018363B2

Reaction notes

Loading…