Hexane → HCID 22349981, compound

HRID 896236Notes

Reaction equation

HRID 896236 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][CH2:6][C:7]1[N:12]=[C:11]([Cl:13])[CH:10]=[C:9](Cl)[N:8]=1.C[Si](C)(C)[N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1.[F-].[Cs+].CCCCCC>CN(C=O)C.C(OCC)(=O)C>[Cl:13][C:11]1[CH:10]=[C:9]([N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)[N:8]=[C:7]([CH2:6][CH2:5][C:4]2[CH:15]=[CH:16][CH:17]=[C:2]([Cl:1])[CH:3]=2)[N:12]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 25953Cesium fluorideHCID 28925(Trimethylsilyl)imidazoleHCID 223499884,6-Dichloro-2-[2-(3-chlorophenyl)ethyl]pyrimidine

Product 1

HCID 22349981HCID 22349981, compoundYield 62.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(3-chlorophenethyl)-4,6-dichloropyrimidine (286 mg, 1 mmol) 91 in 3 mL of dry DMF was treated with 1-trimethylsilylimidazole (140 mg, 1 mmol) and CsF (152 mg, 1 mmol) at RT overnight. Aqueous work up and chromatography (silica gel, hexane:ethyl acetate, 1:1) gave 200 mg of 4-chloro-2-(3-chlorophenethyl)-6-(1-imidazolyl)pyrimidine (92).

Sources & evidence

ORD record
ord-d9b23acd093448ae9e4dfab5e50c9c62
Source dataset
uspto-grants-2005_07
Patent number
US06919347B2

Reaction notes

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