Methylamine → [4-(2-Chloro-pyridin-3-yl)-[1,3,5]triazin-2-yl]-methyl-amine

HRID 227739Notes

Reaction equation

HRID 227739 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)[N:5]=[CH:4][N:3]=1.[CH3:15][NH2:16]>C(Cl)Cl.C1COCC1.CC(C)=O>[Cl:14][C:9]1[C:8]([C:6]2[N:5]=[CH:4][N:3]=[C:2]([NH:16][CH3:15])[N:7]=2)=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

6

Reactant 2

HCID 6329MethylamineHCID 161089782-Chloro-4-(2-chloro-pyridin-3-yl)-[1,3,5]triazine

Product 1

HCID 16108979[4-(2-Chloro-pyridin-3-yl)-[1,3,5]triazin-2-yl]-methyl-amine

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 2-chloro-4-(2-chloro-pyridin-3-yl)-[1,3,5]triazine (10.0 g, 44.0 mmol) in 55 ml of methylene chloride was added methylamine (45 ml, 88.0 mmol) as a 2.0 M solution in THF at 0° C. After stirring at room temperature for 18 h, the mixture was diluted with acetone and filtered through a plug of silica gel and concentrated to yield the desired product. MS m/z=222 [M+H]+. Calc'd for C9H8ClN5: 221.65.

Workup

  1. filtrationfiltered through a plug of silica gel
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7b2f896d57f8429493da92197aa00171
Source dataset
uspto-grants-2009_07
Patent number
US07560551B2

Reaction notes

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