O,O-Dipyridin-2-yl carbonothioate → 4-(2-(4-Isothiocyanatophenoxy)pyridin-3-yl)-2-(methylthio)pyrimidine

HRID 252647

Reaction equation

HRID 252647 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[C:10]([O:15][C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][N:4]=1.[C:23](=[S:38])(OC1C=CC=CN=1)OC1C=CC=CN=1>C(Cl)Cl>[N:22]([C:19]1[CH:18]=[CH:17][C:16]([O:15][C:10]2[C:9]([C:7]3[CH:6]=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:8]=3)=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:21][CH:20]=1)=[C:23]=[S:38]

Participants

4

Reactant 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 667319134-{3-[2-(Methylthio)pyrimidin-4-yl]pyridin-2-yloxy}benzeneamine

Product 1

HCID 866149574-(2-(4-Isothiocyanatophenoxy)pyridin-3-yl)-2-(methylthio)pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A dry 100 ml round bottom flask, under nitrogen, was charged with 4-(3-(2-(methylthio)pyrimidin-4-yl)pyridin-2-yloxy) benzenamine (1.72 g, 5.54 mmol), O,O-dipyridin-2-yl carbonothioate (1.35 g, 5.82 mmol), and DCM (37 ml, 0.15 M). The vessel was closed, kept under nitrogen, and mixture stirred at RT for 18 h. The reaction was diluted with 20 ml DCM and washed with water. The organic layer was collected, dried with Na2SO4, filtered, and concentrated to give 4-(2-(4-isothiocyanatophenoxy)pyridin-3-yl)-2-(methylthio)pyrimidine as a yellow solid. MS m/z=353.0 [M+H]+. Calc'd for C17H12N4OS2: 352.43.

Workup

  1. customThe vessel was closed
  2. washwashed with water
  3. customThe organic layer was collected
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-18510a68b2ad4c88bd53eea9c2ff1c02
Source dataset
uspto-grants-2011_01
Patent number
US07868177B2

Linked notes

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