Dimethyl Sulfoxide → HCID 58174083, compound

HRID 339791Notes

Reaction equation

HRID 339791 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.CS(C)=O.Cl[C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][N:27]=1.C([O-])([O-])=O.[K+].[K+]>O>[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:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][N:27]=3)=[CH:16][CH:15]=2)=[N:3][CH:2]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 58174068HCID 58174068, compound

Product 1

HCID 58174083HCID 58174083, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-[2-(pteridin-4-ylamino)ethyl]phenol (270 mg, 1.0 mmol) and dry DMSO (5 mL) was added 2-chloro-5-trifluoromethylpyridine (155 mg, 0.85 mmol) and K2CO3 (280 mg, 2.0 mmol). This mixture was heated to 80° C. for 3 h, cooled to ambient temperature, poured into H2O (20 mL) and extracted with CH2Cl2 (20 mL). The CH2Cl2 solution was washed with H2O (2×10 mL), dried with Na2SO4, and the solution was filtered. The solution was concentrated in vacuo, redissolved in a minimum volume of CH2Cl2 and treated with hexane to precipitate a solid. The solid was collected by filtration and dried under vacuum to afford pteridin-4-yl-{2-[4-(5-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl}-amine (310 mg) as an off-white solid: mp 147-150° C.; 1H NMR (300 MHz, CDCl3) δ 9.04 (d, J=1.9 Hz, 1H), 8.85 (s, 1H), 8.64 (d, J=1.9 Hz, 1H), 8.35 (d, J=5.2 Hz, 1H), 7.40-7.29 (m, 3H), 7.22 (dd, J=5.2, 0.8 Hz, 1H), 7.19-7.05 (m, 3H), 4.01 (dd, J=13.3, 7.0 Hz, 2H), 3.10 (t, J=7.1 Hz, 2H); ESIMS m/z 413 ([M+H]+).

Workup

  1. temperaturecooled to ambient temperature
  2. extractionextracted with CH2Cl2 (20 mL)
  3. washThe CH2Cl2 solution was washed with H2O (2×10 mL)
  4. dry with materialdried with Na2SO4
  5. filtrationthe solution was filtered
  6. concentrationThe solution was concentrated in vacuo
  7. dissolutionredissolved in a minimum volume of CH2Cl2
  8. additiontreated with hexane
  9. customto precipitate a solid
  10. filtrationThe solid was collected by filtration
  11. customdried under vacuum

Sources & evidence

ORD record
ord-93c0e5dc59c6420baa9491d901df5d59
Source dataset
uspto-grants-2014_11
Patent number
US08895568B2

Reaction notes

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