m-Chloroperbenzoic acid → (R)-4-(2-chloro-6-(((R)-methylsulfinyl)methyl)pyrimidin-4-yl)-3-methylmorpholine

(R)-4-(2-Chloro-6-(methylthiomethyl)pyrimidin-4-yl)-3-methylmorpholine (12.63 g, 46.13 mmol) was dissolved in DCM (100 ml), to this was added mCPBA (7.96 g, 46.13 mmol) in one portion and the reaction mixture was stirred for 10 minutes at 25° C. An additional portion of mCPBA (0.180 g) was added. The reaction mixture was quenched with saturated Na2CO3 solution (50 ml) and extracted with DCM (3×50 ml). The organic layer was dried over MgSO4, filtered and then evaporated. The residue was dissolved in DCM (80 ml) in a 150 ml conical flask which was placed into a beaker containing Et2O (200 ml) and the system covered with laboratory film and then left for 3 days. The obtained crystals were filtered, crushed and sonicated with Et2O. The crystallisation procedure was repeated to afford (R)-4-(2-chloro-6-((R)-methylsulfinylmethyl)pyrimidin-4-yl)-3-methylmorpholine as white needles (3.87 g, 29%); 1H NMR (400 MHz, CDCl3) 1.33 (3H, d), 2.62 (3H, s), 3.30 (1H, td), 3.53 (1H, td), 3.68 (1H, dd), 3.76 (2H, dd), 3.95 (1H, d), 4.00 (1H, dd), 4.02 (1H, s), 4.32 (1H, s), 6.42 (1H, s).

1. customThe reaction mixture was quenched with saturated Na2CO3 solution (50 ml)
2. extractionextracted with DCM (3×50 ml)
3. dry with materialThe organic layer was dried over MgSO4
4. filtrationfiltered
5. customevaporated
6. dissolutionThe residue was dissolved in DCM (80 ml) in a 150 ml conical flask which
7. additioncontaining Et2O (200 ml)
8. waitleft for 3 days
9. filtrationThe obtained crystals were filtered
10. customcrushed
11. customsonicated with Et2O
12. customThe crystallisation procedure

ORDレコード

ord-a4b7ab2bf4b642bcae2e36c76be79235

出典データセット

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09421213B2