Tetrabutylammonium Fluoride → HCID 57504493, compound

HRID 1098000Notes

Reaction equation

HRID 1098000 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][CH2:28][CH2:29][C@H:30]([O:41][C:42]1[N:47]=[CH:46][N:45]=[C:44]2[N:48]([C:51]3[C:56]([Cl:57])=[CH:55][CH:54]=[CH:53][N:52]=3)[N:49]=[CH:50][C:43]=12)[C:31]([NH:33][C:34]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][N:35]=1)=[O:32])(C(C)(C)C)(C)C>C1COCC1>[Cl:57][C:56]1[C:51]([N:48]2[C:44]3[N:45]=[CH:46][N:47]=[C:42]([O:41][C@@H:30]([CH2:29][CH2:28][CH2:27][OH:26])[C:31]([NH:33][C:34]4[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][N:35]=4)=[O:32])[C:43]=3[CH:50]=[N:49]2)=[N:52][CH:53]=[CH:54][CH:55]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57504494HCID 57504494, compound

Product 1

HCID 57504493HCID 57504493, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tetrabutylammonium fluoride 2M in THF (0.449 mL, 0.45 mmol) was added in one portion to a stirred solution of (2S)-5-(tert-butyldimethylsilyloxy)-2-(1-(3-chloropyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-N-(5-methylpyridin-2-yl)pentanamide (Intermediate O1) (170 mg, 0.30 mmol) in THF (5 mL). The resulting solution was stirred at ambient temperature for 4 hours, evaporated and the residue dissolved in ethyl acetate (30 mL). This was washed with water (20 mL) and brine (20 mL), dried (MgSO4) and evaporated. The residue was purified by flash silica chromatography, eluting with 0 to 10% MeOH in ethyl acetate to afford the product (100 mg, 73%). 1H NMR (400 MHz, CDCl3) δ 1.61-1.68 (1H, m), 1.84-1.88 (2H, m), 2.23-2.36 (2H, m), 2.30 (3H, s), 3.72-3.82 (2H, m), 5.94-5.98 (1H, m), 7.46 (1H, dd), 7.54 (1H, dd), 8.01 (1H, dd), 8.08-8.10 (1H, m), 8.12-8.15 (1H, m), 8.45 (1H, s), 8.61-8.62 (2H, m), 8.63 (1H, s); m/z (ESI+)(M+H)+=454; HPLC tR=1.51 min.

Workup

  1. customevaporated
  2. dissolutionthe residue dissolved in ethyl acetate (30 mL)
  3. washThis was washed with water (20 mL) and brine (20 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by flash silica chromatography
  7. washeluting with 0 to 10% MeOH in ethyl acetate

Sources & evidence

ORD record
ord-e3e7abd3d2bf4360a6c867e294abe512
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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