Dimethyl Sulfoxide → 6-(2-chloropyridin-3-yl)-N-methylpyrimidin-4-amine

HRID 1361669Notes

Reaction equation

HRID 1361669 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:9]([Cl:14])=[N:10][CH:11]=[CH:12][CH:13]=2)[N:5]=[CH:4][N:3]=1.Cl.[CH3:16][NH2:17].C([O-])([O-])=O.[K+].[K+].CS(C)=O>O>[Cl:14][C:9]1[C:8]([C:6]2[N:5]=[CH:4][N:3]=[C:2]([NH:17][CH3:16])[CH:7]=2)=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 6364545Methylamine hydrochlorideHCID 249021514-Chloro-6-(2-chloro-pyridin-3-yl)-pyrimidine

Product 1

HCID 589422526-(2-chloropyridin-3-yl)-N-methylpyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

4-Chloro-6-(2-chloro-pyridin-3-yl)-pyrimidine (450 mg, 1.99 mmol), methylamine hydrochloride (202 mg, 2.99 mmol), K2CO3 (550 mg, 3.98 mmol) and DMSO (3.0 mL) were combined. The mixture was heated overnight at 80° C. in a sealed tube. The cooled mixture was diluted with water (300 mL) and the resulting solid was filtered, washed with water and dried to yield the title compound. MS m/z=221 [M+1]+. Calc'd for C10H9ClN4: 220.66.

Workup

  1. filtrationthe resulting solid was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-b14af696e02f4cf3aad60a66c301aa91
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

Loading…