Hexamethyldisilazane → HCID 51000640, compound

HRID 1255878

Reaction equation

HRID 1255878 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-39265cdc796e43df9855786b66e2bf2b
Source dataset
uspto-grants-2013_06
Patent number
US08461164B2

Linked notes

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