1,2-Dibromoethane → HCID 71257370, compound

Participants

Reaction Conditions

Reaction Steps

Methyl [6-(1,4-dioxaspiro[4.5]dec-8-yloxy)-2-(trifluoromethyl)pyrimidin-4-yl]acetate (0.46 g, 1.2 mmol) was dissolved in tetrahydrofuran (23 mL), then 1,2-dibromoethane (300 μL, 3.4 mmol) was added and the reaction mixture cooled to 0° C. NaH in mineral oil (136 mg, 3.4 mmol) was then added and the reaction mixture was heated to 67° C. for 18 h. LCMS showed 50% reaction. The reaction was quenched with saturated NH4Cl and was partitioned between EtOAc and water. The EtOAc extract was washed with brine, dried (Na2SO4), and stripped in vacuo. The ester was purified by automatic silica gel chromatography on a 40 g silica gel column, using solvent A=hexane; solvent B=EtOAc; flow 40 mL/min; A, 2 min; Gradient to 30% B in 30 min; detector set at 254 nm; collected 47 mL fractions; retention time starting ester, 26 min; product, 19 min. The solvent was removed by rotary evaporation to give 0.17 g of product. 1H NMR (300 MHz, CDCl3) δ 7.35 (s, 1H); 5.30 (m, 1H); 3.97 (s, 4H); 3.74 (s, 3H); 1.8-2.0 (m, 6H); 1.6-1.8 (m, 6H).

Provenance & Evidence