2,6-Lutidine → HCID 68594441, compound

HRID 2191020Notes

Reaction equation

HRID 2191020 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH:15]([O:16]C(=O)C3C=CC=CC=3)[CH2:14][CH:13]([CH:25]=[CH:26][P:27]([O:32]CC)([O:29]CC)=[O:28])[O:12]2)=[C:4](Cl)[N:3]=1.C[Si](Br)(C)C.[N:41]1C(C)=CC=CC=1C>CC#N>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[O:12][CH:13]([CH:25]=[CH:26][P:27](=[O:28])([OH:29])[OH:32])[CH2:14][CH:15]2[OH:16])=[C:4]([NH2:41])[N:3]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 76113BromotrimethylsilaneHCID 72247287HCID 72247287, compound

Product 1

HCID 68594441HCID 68594441, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 13.1 (147.5 mg, 0.283 mmol) was dissolved in 3 mL CH3CN, treated with TMSBr (0.3 mL) and 2,6-lutidine (0.075 mL). The mixture was stirred at room temperature for 1.5 h, concentrated and coevaporated with CH3CN under reduced pressure. The residue was dissolved in 30% NH3 in water, and the mixture was stirred at 100° C. for 1.5 h. The mixture was then treated with NaHCO3 (500 mg) and concentrated under reduced pressure. The residue was subjected to reverse phase HPLC eluting with 0-25% CH3CN in water to yield compound 13.2 (81 mg, 74.3% yield). 1H NMR (D2O) δ 2.05-2.25 (m, 2H), 4.58 (m, 1H), 5.8 (d, 1H, J=1.5), 5.95 (m, 1H), 6.15 (m, 1H), 7.8 (s, 1H). 31P NMR (D2O) d 9.15. LRMS (ESI) MH+ C11H15N6O5P requires 343.3. Found 343.1.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in 30% NH3 in water
  3. stirringthe mixture was stirred at 100° C. for 1.5 h
  4. additionThe mixture was then treated with NaHCO3 (500 mg)
  5. concentrationconcentrated under reduced pressure
  6. washHPLC eluting with 0-25% CH3CN in water

Sources & evidence

ORD record
ord-81aae7b63f294997a4f02e97de3d568b
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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