2,6-Lutidine → HCID 86641132, compound

HRID 2191062Notes

Reaction equation

HRID 2191062 reaction equation
C([O:3][P:4]([CH:9]=[CH:10][C:11]1([N:26]=[N+:27]=[N-:28])[CH:15]([OH:16])[CH:14]([OH:17])[CH:13]([N:18]2[CH:23]=[CH:22][C:21](=[O:24])[NH:20][C:19]2=[O:25])[O:12]1)(=[O:8])[O:5]CC)C.N1C(C)=CC=CC=1C.C[Si](Br)(C)C>CC#N>[N:26]([C:11]1([CH:10]=[CH:9][P:4](=[O:3])([OH:8])[OH:5])[CH:15]([OH:16])[CH:14]([OH:17])[CH:13]([N:18]2[CH:23]=[CH:22][C:21](=[O:24])[NH:20][C:19]2=[O:25])[O:12]1)=[N+:27]=[N-:28]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 76113BromotrimethylsilaneHCID 86641130HCID 86641130, compound

Product 1

HCID 86641132HCID 86641132, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 48.5 (119 mg, 0.28 mmol) was dissolved in 2.6 mL CH3CN, treated with 2,6-lutidine (0.1 mL) and TMSBr (0.2 mL). The mixture was stirred at rt for 2 h and concentrated under reduced pressure. The residue was coevaporated with saturated NH4OH three times and the residue was subjected to a reverse phase HPLC to give compound 48.6 (100 mg, 92% yield). 1H NMR (D2O, 300 MHz) 7.45 (d, J=8.1 Hz, 1H), 6.22 (app d, J=8.7 Hz, 1H), 6.16 (app d, J=5.7 Hz, 1H), 5.85 (d, J=3.0 Hz, 1H), 5.71 (d, J=8.1 Hz, 1H), 4.31 (m, 1H), 4.24 (m, 1H); 31P NMR (D2O 121.4 MHz) 7.3; MS (ESI) m/z 359 [M−2H]+.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ac4e608c03974e039e56914355222d25
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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