Dimethylformamide → Dimethyl-carbamic acid 5-chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridin-3-ylmethyl ester
Reaction equation
[Cl:1][C:2]1[C:3]([CH2:10][O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)=[C:4]([CH2:8][OH:9])[CH:5]=[N:6][CH:7]=1.[H-].[Na+].[CH3:20][N:21]([CH:23]=[O:24])[CH3:22]>>[Cl:1][C:2]1[C:3]([CH2:10][O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)=[C:4]([CH2:8][O:9][C:23](=[O:24])[N:21]([CH3:22])[CH3:20])[CH:5]=[N:6][CH:7]=1Participants
4
Procedure
To a solution of [5-chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridin-3-yl]-methanol (0.11 g, 0.43 mmol) and NaH (17 mg, 0.86 mmol) in DMF (3 mL) dimethylcarbamyl chloride (0.39 μL, 2.15 mmol) was added and stirring was continued at RT overnight. Solvents were concentrated in vacuo and the residue was partitioned between EA (10 mL) and saturated NaCl solution (10 mL). After extraction of the aqueous layer with EA (2×10 mL) the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The resulting title compound was used for the next reaction without purification. MS (m/z): 328.9 [M+H+].