Water → HCID 58174114, compound

HRID 339793Notes

Reaction equation

HRID 339793 reaction equation
F[C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH:17][C:18]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][N:26]=4)[N:21]=[CH:20][N:19]=3)=[CH:11][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:28][O-:29].[Na+].O>CS(C)=O>[CH3:28][O:29][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH:17][C:18]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][N:26]=4)[N:21]=[CH:20][N:19]=3)=[CH:11][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 58174220HCID 58174220, compound

Product 1

HCID 58174114HCID 58174114, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
25 °C

Procedure

{2-[4-(6-Fluoropyridin-2-yloxy)-phenyl]-ethyl}-pteridin-4-ylamine (200 mg, 0.55 mmol) was dissolved in 4 mL dry DMSO and treated with sodium methoxide (300 mg, 5.5 mmol, 10 eq) and stirred for 20 h at 25° C. The mixture was poured into H2O (15 mL) and extracted with CH2Cl2 (2×25 ml). The pooled CH2Cl2 extracts were washed with H2O and brine, dried (Na2SO4), filtered, and evaporated. The gummy residue was dissolved in a minimum quantity of CH2Cl2 and treated with hexane to precipitate the product as a solid that was collected by suction filtration, washed with hexane and dried in vacuo to afford {2-[4-(6-methoxypyridin-2-yloxy)-phenyl]-ethyl}-pteridin-4-yl-amine (139 mg) as a tan solid: mp 152-153° C.; 1H NMR (DMSO-d6) δ 9.09 (s, 1H), 9.00 (t, J=5.9 Hz, 1H), 8.82 (s, 1H), 8.63 (s, 1H), 7.70 (t, J=8.0 Hz, 1H), 7.30 (d, J=8.3 Hz, 2H), 7.05 (d, J=8.4 Hz, 2H), 6.51 (d, J=8.0 Hz, 2H), 6.36 (d, J=7.7 Hz, 2H), 3.83 (m, 2H), 3.65 (s, 3H), 3.00 (m, 2H); ESIMS m/z 375 ([M+H]+).

Workup

  1. extractionextracted with CH2Cl2 (2×25 ml)
  2. washThe pooled CH2Cl2 extracts were washed with H2O and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe gummy residue was dissolved in a minimum quantity of CH2Cl2
  7. additiontreated with hexane
  8. customto precipitate the product as a solid
  9. filtrationthat was collected by suction filtration
  10. washwashed with hexane
  11. customdried in vacuo

Sources & evidence

ORD record
ord-90c513abf303479fb5157bf7399db8a7
Source dataset
uspto-grants-2014_11
Patent number
US08895568B2

Reaction notes

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