2,6-Lutidine → HCID 25005299, compound

HRID 1175674Notes

Reaction equation

HRID 1175674 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:15][C@:14]([CH3:26])([O:16][CH2:17][P:18](=[O:25])([O:22]CC)[O:19]CC)[C@@H:13]([OH:27])[C@H:12]1[OH:28].N1C(C)=CC=CC=1C.C[Si](I)(C)C>C(#N)C>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:15][C@:14]([CH3:26])([O:16][CH2:17][P:18](=[O:19])([OH:22])[OH:25])[C@@H:13]([OH:27])[C@H:12]1[OH:28]

Participants

5

Reactant 3

HCID 79372,6-Lutidine2×HCID 85247Trimethylsilyl iodideHCID 25005654HCID 25005654, compound

Product 1

HCID 25005299HCID 25005299, compoundYield 397.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of compound 31.4 (20 mg, 0.048 mmol) in acetonitrile (2 mL) was added 2,6-lutidine (0.034 mL, 0.29 mmol) and then trimethylsilyl iodide (0.068 mL, 0.48 mmol). The mixture was stirred at room temperature for 1 h. After the reaction was done, 0.08 mL of 2,6-lutidine was added to the mixture and the mixture was concentrated under reduced pressure. The residue was then put into solution with water (2 mL) and treated with sodium hydroxide 1N to pH=10. The solution was then acidify to pH=3 using acetic acid and subjected to a reverse phase (YMC-Pack ODS-A) to give compound 31.5 (69 mg, 72% yield). 1H NMR (300 MHz, D2O): δ 1.42 (s, 3H), 3.33 (t, 1H, J=10.7), 3.51 (t, 1H, J=11.9), 4.12 (d, 1H, J=4.6), 5.18 (m, 1H), 6.10 (d, 1H, J=7.1), 8.24 (s, 1H), 8.55 (s, 1H). LRMS (ESI) MH+ C11H16N5O7P requires 362.3. Found 361.9.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additiontreated with sodium hydroxide 1N to pH=10

Sources & evidence

ORD record
ord-d47bfbca48e94dafb36d21f3007ec15c
Source dataset
uspto-grants-2010_11
Patent number
US07842672B2

Reaction notes

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