HCID 59232122, compound → HCID 59232090, compound

HRID 1099294Notes

Reaction equation

HRID 1099294 reaction equation
[Si:1]([O:8][CH2:9][CH2:10]/[CH:11]=[CH:12]/[C:13]1[N:21]2[C:16]([C:17]([NH2:22])=[N:18][CH:19]=[N:20]2)=[CH:15][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(O)(=O)C.[Pt](=O)=O>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[N:21]2[C:16]([C:17]([NH2:22])=[N:18][CH:19]=[N:20]2)=[CH:15][CH:14]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 59232122HCID 59232122, compound

Product 1

HCID 59232090HCID 59232090, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

To a dry flask purged with N2 was added platinum(IV) oxide (635 mg, 2.80 mmol) followed by 7-((1E)-4-{[tert-butyl(dimethyl)silyl]oxy}but-1-en-1-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (6.35 g, 19.9 mmol) as a solution in acetic acid (100 mL). The mixture was stirred under an H2 atmosphere for 16 h. The mixture was filtered through a pad of Celite® rinsing with acetic acid. The solvent was evaporated under reduced pressure and the residue was made basic with saturated aqueous NaHCO3 solution. The resulting solid was collected by filtration and dried in vacuo to afford 5.6 g (88%) of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 7.76 (s, 1 H), 7.52 (br s, 2 H), 6.77 (d, 1 H), 6.38 (d, 2 H), 3.57 (t, 2 H), 2.82 (t, 2 H), 1.74-1.62 (m, 2 H), 1.54-1.43(m, 2 H), 0.83 (s, 9 H), 0.00 (s, 6 H); ES-MS m/z 321.2 [M+H]+, HPLC RT (min) 3.11.

Workup

  1. customTo a dry flask purged with N2
  2. filtrationThe mixture was filtered through a pad of Celite®
  3. washrinsing with acetic acid
  4. customThe solvent was evaporated under reduced pressure
  5. filtrationThe resulting solid was collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-e2767d07a93d42c989904e6dd7a3d308
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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