Trifluoroacetic acid → [4-(2-Chloro-pyridin-3-yl)-5-fluoro-pyrimidin-2-yl]-methyl-amine

HRID 1361653Notes

Reaction equation

HRID 1361653 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([Cl:14])=[N:10][CH:11]=[CH:12][CH:13]=2)[C:5]([F:15])=[CH:4][N:3]=1.Cl.[CH3:17][NH2:18].C([O-])([O-])=O.[K+].[K+].C(O)(C(F)(F)F)=O>CCOC(C)=O.O.CS(C)=O>[Cl:14][C:9]1[C:8]([C:6]2[C:5]([F:15])=[CH:4][N:3]=[C:2]([NH:18][CH3:17])[N:7]=2)=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 6364545Methylamine hydrochlorideHCID 772302032-Chloro-4-(2-chloro-pyridin-3-yl)-5-fluoro-pyrimidine

Product 1

HCID 86602592[4-(2-Chloro-pyridin-3-yl)-5-fluoro-pyrimidin-2-yl]-methyl-amine

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

To 2-chloro-4-(2-chloro-pyridin-3-yl)-5-fluoro-pyrimidine (178 mg, 0.73 mmol) and methylamine hydrochloride (74 mg, 1.1 mmol) was added K2CO3 (202 mg, 1.46 mmol) and DMSO (1.5 mL). The mixture was heated overnight in a sealed tube at 55° C. The mixture was cooled to RT, diluted with EtOAc and water, then neutralized with TFA (pH˜6-7). The organic layer was washed several times with water, dried over Na2SO4, filtered and concentrated to yield [4-(2-chloro-pyridin-3-yl)-5-fluoro-pyrimidin-2-yl]-methyl-amine. MS m/z=239 [M+1]+. Calc'd for C10H8ClFN4: 238.65.

Workup

  1. temperatureThe mixture was cooled to RT
  2. washThe organic layer was washed several times with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-33a23b78f0994e8fa8f1a88d70f2b605
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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