Pyridine, hydrofluoride (1:1) → HCID 66797935, compound

HRID 1677970Notes

Reaction equation

HRID 1677970 reaction equation
[Si]([O:8][CH2:9][C@@H:10]1[C@H:14]2[O:15][C:16]([CH3:19])([CH3:18])[O:17][C@H:13]2[C@H:12]([NH:20][C:21]2[CH:26]=[C:25]([C:27]#[C:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:24]=[CH:23][N:22]=2)[CH2:11]1)(C(C)(C)C)(C)C.F.N1C=CC=CC=1>C1COCC1.N1C=CC=CC=1>[CH3:18][C:16]1([CH3:19])[O:17][C@H:13]2[C@H:12]([NH:20][C:21]3[CH:26]=[C:25]([C:27]#[C:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:24]=[CH:23][N:22]=3)[CH2:11][C@H:10]([CH2:9][OH:8])[C@H:14]2[O:15]1

Participants

5

Reactant 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 66797908HCID 66797908, compound

Product 1

HCID 66797935HCID 66797935, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[(3aS,4R,6R,6aR)-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-6-(phenylethynyl)pyrimidin-4-amine (0.275 g, 0.573 mmol) in THF (2 mL) and pyridine (2 mL) in a teflon vial was added pyridine hydrofluoride (1.3 mL, 0.014 mol) dropwise. The reaction was stirred for 1.5 h then quenched using a saturated aqueous Na2CO3 solution (15 mL) and EtOAc. The aqueous layer was extracted with EtOAc (3×20 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography (0 to 5% MeOH/EtOAc) to afford the title compound as a yellow solid (0.172 g, 82%). LC/MS: Rt=1.29 min, ES+ 366 (FA standard).

Workup

  1. customthen quenched
  2. extractionThe aqueous layer was extracted with EtOAc (3×20 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (0 to 5% MeOH/EtOAc)

Sources & evidence

ORD record
ord-464b6a58526344ec9168180e6600c60f
Source dataset
uspto-grants-2011_08
Patent number
US08008307B2

Reaction notes

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