反应详情

1-Chloro-N,N,2-trimethylprop-1-en-1-amine (0.170 mL, 1.28 mmol) was added to a stirred solution of (S)-2-(tert-butyldimethylsilyloxy)-3-((R)-1-methoxypropan-2-yloxy)propanoic acid (Intermediate Y10) (250 mg, 0.85 mmol) in DCM (5 mL) at room temperature under nitrogen. The resulting solution was stirred at room temperature for 30 minutes. A solution of 5-methylpyrazin-2-amine (140 mg, 1.28 mmol) in DCM (5 mL) was added to the reaction mixture and the resulting solution was stirred at room temperature for 16 hours. The reaction mixture was quenched with water (20 mL), extracted with DCM (2×25 mL), the combined organic layers were dried (MgSO4) and evaporated. The crude product was purified by flash silica chromatography, eluting with 0 to 90% ethyl acetate in isohexane to afford the product (170 mg, 51.8%). 1H NMR (400 MHz, DMSO) δ 0.01 (d, 6H), 0.80 (s, 9H), 0.91 (d, 3H), 2.35 (s, 3H), 3.09-3.23 (m, 5H), 3.47-3.63 (m, 3H), 4.35-4.40 (m, 1H), 8.20 (s, 1H), 9.09 (s, 1H), 9.63 (s, 1H); m/z (ESI+) (M+H)+=384.43; HPLC tR=2.99 min.

1. stirringthe resulting solution was stirred at room temperature for 16 hours
2. customThe reaction mixture was quenched with water (20 mL)
3. extractionextracted with DCM (2×25 mL)
4. dry with materialthe combined organic layers were dried (MgSO4)
5. customevaporated
6. customThe crude product was purified by flash silica chromatography
7. washeluting with 0 to 90% ethyl acetate in isohexane