Hexamethyldisilazane → HCID 51000640, compound

HRID 339789

Reaction equation

HRID 339789 reaction equation
[N:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][N:9]=2)[C:4](O)=[N:3][CH:2]=1.[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][NH2:28])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C[Si](C)(C)N[Si](C)(C)C.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][CH2:27][NH:28][C:4]2[C:5]3[C:10](=[N:9][CH:8]=[CH:7][N:6]=3)[N:1]=[CH:2][N:3]=2)=[CH:24][CH:25]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 4

HCID 13838HexamethyldisilazaneHCID 2009572-(4-Benzyloxy-phenyl)-ethylamineHCID 6097028Ammonium SulfateHCID 178518044HCID 178518044, compound

Product 1

HCID 51000640HCID 51000640, compoundYield 73.8%

Conditions

Temperature
114 °C

Procedure

To a mixture of pteridin-4-ol (282 mg, 1.9 mmol) and 2-(4-benzyloxyphenyl)-ethylamine (476 mg, 2.1 mmol) and hexamethyldisilazane (5 mL) in a 25 mL round bottom flask, equipped with reflux condenser, drying tube and magnetic stir bar, was added ammonium sulfate (100 mg, 0.76 mmol). The mixture was heated to 114° C. overnight and then the solvent was removed in vacuo. The residue was suspended in H2O and filtered. The filter cake was dissolved in CH2Cl2, dried with Na2SO4, filtered, and concentrated in vacuo to provide [2-(4-benzyloxyphenyl)-ethyl]-pteridin-4-yl-amine as a white solid (501 mg): 1H NMR (300 MHz) δ 9.01 (d, J=1.9 Hz, 1H), 8.81 (s, 1H), 8.61 (d, J=1.9 Hz, 1H), 7.49-7.29 (m, 6H), 7.25-7.15 (m, 3H), 6.96 (dd, J=6.8, 4.8 Hz, 2H), 5.06 (s, 2H), 3.93 (dd, J=13.2, 6.9 Hz, 2H), 3.00 (t, J=7.0 Hz, 2H); ESIMS m/z 358.1 ([M+H]+).

Workup

  1. customequipped
  2. temperaturewith reflux condenser
  3. customdrying tube and magnetic stir bar
  4. customthe solvent was removed in vacuo
  5. filtrationfiltered
  6. dissolutionThe filter cake was dissolved in CH2Cl2
  7. dry with materialdried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-77c73c745c1c4686897b5f10ee01b42b
Source dataset
uspto-grants-2014_11
Patent number
US08895568B2

Linked notes

Loading…