Sodium Carbonate → 4-(3,5-Difluoro-phenyl)-2,6-dimethyl-pyrimidine

HRID 552491Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH3:9])[N:3]=1.[F:10][C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[C:15]([F:17])[CH:16]=1.[F-].[K+].C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O>[F:10][C:11]1[CH:12]=[C:13]([C:2]2[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH3:9])[N:3]=2)[CH:14]=[C:15]([F:17])[CH:16]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a suspension of 8.0 g, (43 mmol) of 4-Bromo-2,6-dimethyl-pyrimidine [CAS 354574-56-4], 8.1 g (51 mmol, 1.2 equiv.) of 3,5-Difluorophenylboronic acid, an 1.917 g (33.0 mmol, 3.3 equiv.) of KF in 80 ml of DME were added 20 ml of 2M sodium carbonate solution and the mixture was purged with Argon for 10 min. Then 2.24 g (8.6 mmol, 0.2 equiv.) of Triphenylphosphine and 0.96 g (4.3 mmol, 0.1 equiv.) of Palladium acetate were added and the mixture was stirred under Argon atmosphere for 18 h at 85° C. The reaction was allowed to cool to r.t., and worked up with ethyl acetate/water. The crude material was purified by flash chromatography on silicagel (heptane/ethyl acetate 1:1) to yield the title compound (1.96 g, 21%) as a red solid, MS (ISP): m/e=221.2 (M+H)+.

Workup

customthe mixture was purged with Argon for 10 min
temperatureto cool to r.t.
customThe crude material was purified by flash chromatography on silicagel (heptane/ethyl acetate 1:1)

Sources & evidence

ORD record: ord-bb363a9efa514d4681daff64df07be48
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951824B2

Reaction notes

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