Methylamine → HCID 86703042, compound

HRID 1851228Notes

Reaction equation

HRID 1851228 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6](Cl)[N:5]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[N:17]=[C:4]2[N:3]=1.[CH3:24][NH2:25]>CN(C=O)C.C1COCC1>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([NH:25][CH3:24])[N:5]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[N:17]=[C:4]2[N:3]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 86690304HCID 86690304, compound

Product 1

HCID 86703042HCID 86703042, compoundYield 26.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

1 g (2.9 mmol) 5,7-dichloro-6-phenyl-2-pyridine-2-yl-[1,2,4]triazolo[1,5-a]pyrimidine are given in 8.2 mL DMF (no complete dissolution). After addition of 3.65 mL of a 2M (7.3 mmol) solution of methylamine in THF the reaction mixture is heated in a microwave oven at 100° C. for 20 minutes. From the clear brown solution the DMF is evaporated, the residue is diluted with brine and extracted three times with dichloromethane. The combined organic extracts are dried over Na2SO4 and the solvent is evaporated and the residue purified by chromatography (silicagel, eluents: dichloromethane, methanol). 265 mg (26.9%) of the desired product are obtained.

Workup

  1. dissolutionno complete dissolution)
  2. customFrom the clear brown solution the DMF is evaporated
  3. additionthe residue is diluted with brine
  4. extractionextracted three times with dichloromethane
  5. dry with materialThe combined organic extracts are dried over Na2SO4
  6. customthe solvent is evaporated
  7. customthe residue purified by chromatography (silicagel, eluents: dichloromethane, methanol)

Sources & evidence

ORD record
ord-aaf4edd4abc44344be8b1ac29c368965
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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