Sodium hydride → HCID 68733724, compound

Participants

Reaction Steps

To a mixture of NaH (100 mg, 4 mmol) and anhydrous THF (8 mL) was added dropwise a solution of crude methyl (S)-3-amino-3-(4-fluorophenyl)hex-5-enyl((S)-1-(4-bromophenyl)ethyl)carbamate (39 mg, 0.1 mmol) in anhydrous THF (8 mL) at 0° C. The reaction mixture was refluxed overnight. The reaction mixture was quenched with methanol in an ice bath and evaporated to leave a residue, which was dissolved in CH2Cl2. The combined organic phase was dried, filtered and concentrated to give the crude product, which was purified by TLC to provide (S)-4-allyl-1-((S)-1-(4-bromophenyl)ethyl)-4-(4-fluorophenyptetrahydropyrimidin-2(1H)-one (1.2 mg, 3%). LC-MS Method 1 tR=1.603 min, m/z=419; 1H NMR (CD3OD) 1.36 (d, 3H), 1.81-1.92 (m, 1H), 2.16-2.22 (m, 1H), 2.46-2.53 (m, 1H), 2.61-2.84 (m, 3H), 5.12-5.19 (m, 1H), 5.56-5.69 (m, 1H), 7.06-7.13 (m, 2H), 7.18-7.24 (m, 2H), 7.22-7.29 (m, 2H), 7.42-7.51 (m, 2H).

Provenance & Evidence