Ammonium Hydroxide → HCID 68593441, compound

HRID 2191066Notes

Reaction equation

HRID 2191066 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([NH2:35])[C:5]2[N:10]=[N:9][N:8]([CH:11]3[CH:15]([O:16]C(=O)C4C=CC=CC=4)[CH2:14][CH:13]([CH:25]=[CH:26][P:27]([O:32]CC)([O:29]CC)=[O:28])[O:12]3)[C:6]=2[N:7]=1.[Si](Br)(C)(C)C.[NH4+].[OH-]>CC#N.CO>[NH2:1][C:2]1[N:3]=[C:4]([NH2:35])[C:5]2[N:10]=[N:9][N:8]([CH:11]3[O:12][CH:13]([CH:25]=[CH:26][P:27](=[O:28])([OH:29])[OH:32])[CH2:14][CH:15]3[OH:16])[C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 76113Bromotrimethylsilane2×HCID 72247365HCID 72247365, compound

Product 1

HCID 68593441HCID 68593441, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

Compound 53.1 (183 mg, 0.36 mmol) was dissolved in 7 mL of anhydrous CH3CN and treated with TMS—Br (240 uL, 1.82 mmol). The solution was stirred at rt for 6 hrs. Added more TMS—Br (100 uL, 0.75 mmol) and stirred at room temperature for 16 hrs. Concentrated the reaction under reduced pressure. The residue was dissolved in methanol and added aqueous NH4OH solution, stirred for another 3 hrs and concentrated under reduced pressure. The residue was subjected to a reverse phase HPLC to give compound 53.2 (110 mg, 81% yield). 1H NMR (D2O, 300 MHz): δ 6.32 (m, 1H), 6.07 (s, 1H), 5.83 (m, 1H), 4.96 (m, 1H), 4.73 (m, 1H), 2.27 (m, 2H). 31P NMR: 11.17 ppm LC/MS: C10H14N7O5P Exact Mass: 343.08. Found: [M−H]− 342.0, [M+H]+ 344.1.

Workup

  1. stirringstirred at room temperature for 16 hrs
  2. concentrationConcentrated
  3. customthe reaction under reduced pressure
  4. stirringstirred for another 3 hrs
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c36fd45aad7c493dad152262a95991b5
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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