Cesium fluoride → HCID 60148745, compound

HRID 876519Notes

Reaction equation

HRID 876519 reaction equation
[N:1]1([C:7]2[N:8]=[C:9]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[C:10]3[CH:15]=[C:14]([C:16]4[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=4)[N:13](COCC[Si](C)(C)C)[C:11]=3[N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F-].[Cs+]>CC(C)=O>[N:1]1([C:7]2[N:8]=[C:9]([N:31]3[CH2:32][CH2:33][O:34][CH2:35][CH2:36]3)[C:10]3[CH:15]=[C:14]([C:16]4[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=4)[NH:13][C:11]=3[N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 68194851HCID 68194851, compound

Product 1

HCID 60148745HCID 60148745, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

To a round bottom flask were added 3-[2,4-di-morpholin-4-yl-7-(2-trimethylsilanyl-ethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenol (8.1 mg, 0.016 mmol) and cesium fluoride (72.4 mg, 0.477 mmol, 30 equiv) followed by acetone (6 mL). The reaction was heated for 6 hours at 40° C. The reaction was then quenched by adding aqueous saturated ammonium chloride solution (10 mL). Acetone was removed under reduced pressure and the aqueous phase was extracted with DCM (3×15 mL). The combined organic phase was removed under reduced pressure and the crude product was directly purified using reverse phase preparative HPLC (5% to 70% H2O/MeCN, with n-propanol in water as modifier) to obtain the desired product as a white solid (4.1 mg, 67.8% yield). LC/MS analysis method 7, mass (ES+) m/z 382.4, retention time 1.05 min 1HNMR (CDCl3): δ 10.15 (1H, brs), 7.15 (1H, t), 7.02 (1H, d), 6.67 (1H, brs), 6.65 (2H, m), 6.52 (1H, s), 3.82 ppm (8H, dt), 3.64 (8H, m)

Workup

  1. customThe reaction was then quenched
  2. additionby adding aqueous saturated ammonium chloride solution (10 mL)
  3. customAcetone was removed under reduced pressure
  4. extractionthe aqueous phase was extracted with DCM (3×15 mL)
  5. customThe combined organic phase was removed under reduced pressure
  6. customthe crude product was directly purified

Sources & evidence

ORD record
ord-ef67a88078994b5abe461b3fa26213a7
Source dataset
uspto-grants-2015_03
Patent number
US08987257B2

Reaction notes

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