Tributylamine → HCID 86619862, compound

HRID 1024835Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[N:3]=1.[CH3:19][C:20]1([CH3:27])[O:24][CH:23]([CH:25]=[CH2:26])[CH2:22][O:21]1.C(N(CCCC)CCCC)CCC>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=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.[Pd].[Pd]>[Cl:8][C:6]1[CH:7]=[C:2]([CH:26]=[CH:25][CH:23]2[CH2:22][O:21][C:20]([CH3:27])([CH3:19])[O:24]2)[N:3]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[N:5]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4,6-dichloro-2-[(2,3-difluorobenzyl)thio]pyrimidine (product of example 1 step ii) (0.5 g), tris(dibenzylideneacetone)dipalladium(0) (45 mg), 2,2-dimethyl-4-vinyl-1,3-dioxolane (630 mg), tri-n-butylamine (610 mg) and tetra-n-butylammonium chloride (460 mg) in anhydrous N,N-dimethylformamide (6.5 ml) were heated at 90° C. for 3 h. then stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic phase was washed with water and brine, dried (MgSO4) and the solvent evaporated under reduced pressure. The residue was purified by flash silica-gel chromatography eluting with 10% diethyl ether in iso-hexane to give the sub-title compound as a yellow viscous oil. Yield: 98 mg.

Workup

customThe reaction mixture was partitioned between ethyl acetate and water
washThe organic phase was washed with water and brine
dry with materialdried (MgSO4)
customthe solvent evaporated under reduced pressure
customThe residue was purified by flash silica-gel chromatography
washeluting with 10% diethyl ether in iso-hexane

Sources & evidence

ORD record: ord-db4dfe1438da44059dc9217b2701f941
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722883B2

Reaction notes

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