Tetrabutylammonium Fluoride → HCID 86696683, compound

HRID 2365829Notes

Reaction equation

HRID 2365829 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][CH:28]([N:36]1[CH:41]=[CH:40][C:39]([C:42]2[C:47]([F:48])=[CH:46][N:45]=[C:44]([NH:49][CH:50]3[CH2:55][CH2:54][O:53][CH2:52][CH2:51]3)[N:43]=2)=[CH:38][C:37]1=[O:56])[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=1)(C(C)(C)C)(C)C>C1COCC1>[Cl:35][C:31]1[CH:30]=[C:29]([CH:28]([N:36]2[CH:41]=[CH:40][C:39]([C:42]3[C:47]([F:48])=[CH:46][N:45]=[C:44]([NH:49][CH:50]4[CH2:55][CH2:54][O:53][CH2:52][CH2:51]4)[N:43]=3)=[CH:38][C:37]2=[O:56])[CH2:27][OH:26])[CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86696682HCID 86696682, compound

Product 1

HCID 86696683HCID 86696683, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1M Tetrabutylammonium fluoride in THF (0.165 mL, 0.165 mmol) was added to 1-(2-(tert-butyldimethylsilyloxy)-1-(3-chlorophenyl)ethyl)-4-(5-fluoro-2-(tetrahydro-2H-pyran-4-ylamino)pyrimidin-4-yl)pyridin-2(1H)-one (0.0307 g, 0.0549 mmol) in THF (3 mL). The mixture was stirred at room temperature for 30 minutes. The reaction mixture was evaporated, and the residue was partitioned between water and EtOAc. The EtOAc was washed with brine, dried over MgSO4, filtered, and evaporated to yield a crude product as a film. The crude product was purified by chromatography on a 10 g Biotage SNAP column with EtOAc. Fractions 17-32 contained a glass (16.2 mg). The glass was triturated with water and dried to afford 1-(1-(3-chlorophenyl)-2-hydroxyethyl)-4-(5-fluoro-2-((tetrahydro-2H-pyran-4-yl)amino)pyrimidin-4-yl)pyridin-2(1H)-one (0.0129 g, 0.0290 mmol, 52.8% yield) as a film. 1H NMR (400 MHz, CD3OD) δ 8.33 (d, 1H), 7.84 (d, 1H), 7.43-7.24 (m, 5H), 7.03-6.99 (m, 1H), 6.16-6.12 (m, 1H), 4.32-4.27 (m, 1H), 4.22-4.17 (m, 1H), 4.02-3.94 (m, 3H), 3.57-3.49 (m, 2H), 2.02-1.96 (m, 2H), 1.64-1.54 (m, 2H); m/z (APCI-pos) M+1=445.1.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was partitioned between water and EtOAc
  3. washThe EtOAc was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto yield a crude product as a film
  8. customThe crude product was purified by chromatography on a 10 g Biotage SNAP column with EtOAc
  9. customThe glass was triturated with water
  10. customdried

Sources & evidence

ORD record
ord-cc4f646d71434dfbbd57a0162031077e
Source dataset
uspto-grants-2014_04
Patent number
US08697715B2

Reaction notes

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