Dimethylformamide → Dimethyl-carbamic acid 5-chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridin-3-ylmethyl ester

HRID 1959579Notes

Reaction equation

HRID 1959579 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]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 44190475[5-Chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridin-3-yl]-methanol

Product 1

HCID 67077728Dimethyl-carbamic acid 5-chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridin-3-ylmethyl ester

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+].

Workup

  1. concentrationSolvents were concentrated in vacuo
  2. customthe residue was partitioned between EA (10 mL) and saturated NaCl solution (10 mL)
  3. extractionAfter extraction of the aqueous layer with EA (2×10 mL) the combined organic layers
  4. dry with materialwere dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting title compound was used for the next reaction without purification

Sources & evidence

ORD record
ord-510e146f308c41eb839e58b04a23edd4
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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