Triethylamine → HCID 51000641, compound

HRID 339804Notes

Reaction equation

HRID 339804 reaction equation
[N:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][N:9]=2)[C:4]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[N:3][CH:2]=1.[F:21][C:22]1[C:27]([F:28])=[C:26]([C:29]([F:32])([F:31])[F:30])[C:25]([F:33])=[C:24](F)[N:23]=1.CCN(CC)CC>CN(C=O)C>[N:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][N:9]=2)[C:4]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:24]3[C:25]([F:33])=[C:26]([C:29]([F:31])([F:32])[F:30])[C:27]([F:28])=[C:22]([F:21])[N:23]=3)=[CH:16][CH:15]=2)=[N:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10889400Pyridine, 2,3,5,6-tetrafluoro-4-(trifluoromethyl)-HCID 58174068HCID 58174068, compound

Product 1

HCID 51000641HCID 51000641, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[2-(Pteridin-4-ylamino)-ethyl]-phenol (0.27 g, 1.0 mmol), 2,3,5,6-tetrafluoro-4-trifluoromethylpyridine (0.24 g, 1.0 mmol) and DMF (5 mL) were added to a 25 mL round bottom flask equipped with magnetic stirring bar and dry nitrogen line. To the reaction mixture was added Et3N (0.12 g, 1.2 mmol). After stirring 24 h at room temperature, the reaction mixture was concentrated in vacuo, and the residue was partitioned between H2O and EtOAc. The organic layer was concentrated in vacuo and the residue was purified by column chromatography (EtOAc/hexane over SiO2) to afford pteridin-4-yl-{2-[4-(3,5,6-trifluoro-4-trifluoromethyl-pyridin-2-yloxy)-phenyl]-ethyl}-amine (110 mg) as a beige solid: mp 103-108° C.

Workup

  1. customequipped with magnetic stirring bar
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customthe residue was partitioned between H2O and EtOAc
  4. concentrationThe organic layer was concentrated in vacuo
  5. customthe residue was purified by column chromatography (EtOAc/hexane over SiO2)

Sources & evidence

ORD record
ord-7cb7e3c2b449493a9098ff195230c493
Source dataset
uspto-grants-2014_11
Patent number
US08895568B2

Reaction notes

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