Dimethyl Sulfoxide → 4-(2-(4-iodophenoxy)pyridin-3-yl)-N-methylpyrimidin-2-amine

HRID 1361632Notes

Reaction equation

HRID 1361632 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][CH3:15])[N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[I:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>O>[I:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:2]2[C:7]([C:8]3[CH:13]=[CH:12][N:11]=[C:10]([NH:14][CH3:15])[N:9]=3)=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 108944-IodophenolHCID 161090044-(2-chloro-3-pyridinyl)-N-methyl-2-pyrimidinamine

Product 1

HCID 585885464-(2-(4-iodophenoxy)pyridin-3-yl)-N-methylpyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(2-Chloropyridin-3-yl)-N-methylpyrimidin-2-amine (3.30 g, 15.0 mmol), 4-iodophenol (3.96 g, 18.0 mmol), cesium carbonate (10.6 g, 30.0 mmol), and 15 mL of DMSO were added into a 50-mL round bottom flask. The flask was sealed with a septum and placed in a preheated oil bath at 130° C. After 3 h, the reaction was completed according to TLC and LC-MS analysis. The reaction was cooled to room temperature. Water was added into the reaction mixture until all product precipitated out of the solution. The solid was filtered, ground, and washed with water. The product was collected and dried in a vacuum oven overnight. The product, 4-(2-(4-iodophenoxy)pyridin-3-yl)-N-methylpyrimidin-2-amine was obtained as a light brown solid. 1H NMR (Varian, 300 MHz, CDCl3): 8.40 (br s, 1H), 8.34 (d, J=4.1 Hz, 1H), 8.19 (dd, J=4.8, 2.2 Hz, 1H), 7.73 (m, 2H), 7.30 (dd, J=7.4, 4.8 Hz, 1H), 7.19 (m, 2H), 7.00 (m, 2H), 2.84 (d, J=4.8 Hz, 3H).

Workup

  1. customThe flask was sealed with a septum
  2. customplaced in a preheated oil bath at 130° C
  3. customprecipitated out of the solution
  4. filtrationThe solid was filtered
  5. washground, and washed with water
  6. customThe product was collected
  7. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-3f3d8bd4900b43a4912b0c302b95ab99
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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