Methylamine → HCID 17756185, compound

HRID 491658Notes

Reaction equation

HRID 491658 reaction equation
[CH2:1]([O:8][C:9]1[CH:22]=[CH:21][C:12]([O:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16](Cl)[N:15]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][NH2:24]>CS(C)=O>[CH2:1]([O:8][C:9]1[CH:22]=[CH:21][C:12]([O:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH:24][CH3:23])[N:15]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 177554044-(4-Benzyloxy-phenoxy)-2-chloro-pyrimidine

Product 1

HCID 17756185HCID 17756185, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-(4-Benzyloxy-phenoxy)-2-chloro-pyrimidine (Step A, 2.03 g, 6.49 mmol) was dissolved in 10 mL DMSO in a sealed tube at 0° C. 2 N CH3NH2 (in THF) was added (4.9 mL, 9.7 mmol), and the tube was sealed, warmed first to RT for 2 h, then to 70° C. for 2 h with stirring. The reaction was cooled to RT and concentrated in vacuo to a DMSO solution. The crude solution was diluted into Et2O and 1 N NaOH (aq) was added. The layers were separated, and the organic layer was washed several times with water then brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel column chromatography using a hexanes/EtOAc gradient to yield the title compound as a white solid. MS (MH+)=308.3; Calc'd 307.36 for C18H17N3O2.

Workup

  1. customthe tube was sealed
  2. temperatureThe reaction was cooled to RT
  3. concentrationconcentrated in vacuo to a DMSO solution
  4. additionThe crude solution was diluted into Et2O and 1 N NaOH (aq)
  5. additionwas added
  6. customThe layers were separated
  7. washthe organic layer was washed several times with water
  8. dry with materialThe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-692c33e22ca5428aa22ac567fc63c839
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

Loading…