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

HRID 2361032Notes

Reaction equation

HRID 2361032 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].CS(C)=O.Cl[C:20]1[C:25]([C:26]2[CH:31]=[CH:30][N:29]=[C:28]([NH:32][CH3:33])[N:27]=2)=[CH:24][CH:23]=[CH:22][N:21]=1>O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:20]2[C:25]([C:26]3[CH:31]=[CH:30][N:29]=[C:28]([NH:32][CH3:33])[N:27]=3)=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 145104-AminothiophenolHCID 161090044-(2-chloro-3-pyridinyl)-N-methyl-2-pyrimidinamine

Product 1

HCID 577562434-(2-(4-aminophenylthio)pyridin-3-yl)-N-methylpyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

To 4-aminothiophenol (1.70 g, 13.6 mmol) and Cs2CO3 (8.90 g, 27.2 mmol) was added DMSO (18 mL). The mixture was stirred for 5 minutes at 100° C. before 4-(2-chloropyridin-3-yl)-N-methylpyrimidin-2-amine (3.00 g, 13.6 mmol) was added. The resulting mixture was stirred for 16 hours at 130° C., then diluted with water and the resulting solid filtered. After washing the solid with water and Et2O it was dried under vacuum to yield the desired product as a tan solid. MS m/z=310 [M+1]+. Calc'd for C16H15N3S: 309.40.

Workup

  1. additionwas added
  2. filtrationthe resulting solid filtered
  3. washAfter washing the solid with water and Et2O it
  4. customwas dried under vacuum

Sources & evidence

ORD record
ord-109a639f64894f0286bb3b45fcfd57d1
Source dataset
uspto-grants-2014_04
Patent number
US08686155B2

Reaction notes

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