Tetrabutylammonium Fluoride → HCID 44195009, compound

HRID 1878602Notes

Reaction equation

HRID 1878602 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[N:9]=[C:10]([C:17]3[CH:18]=[N:19][CH:20]=[C:21]([C:23]#[C:24][Si](C)(C)C)[CH:22]=3)[C:11]3[CH:16]=[CH:15][NH:14][C:12]=3[N:13]=2)[CH:5]=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:23]([C:21]1[CH:22]=[C:17]([C:10]2[C:11]3[CH:16]=[CH:15][NH:14][C:12]=3[N:13]=[C:8]([C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=3)[N:9]=2)[CH:18]=[N:19][CH:20]=1)#[CH:24]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68934762HCID 68934762, compound2×

Product 1

HCID 44195009HCID 44195009, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(6-methyl-pyridin-2-yl)-4-(5-trimethylsilanylethynyl-pyridin-3-yl)-7H-pyrrolo[2,3-d]pyrimidine (Intermediate 216) (1 eq, 0.181 mmol, 70 mg) in THF (2 ml) is added TBAF (1 M in THF, 2 eq, 0.36 mmol, 0.36 ml). The resulting mixture is stirred for 10 min at r.t., then the solvent is removed in vacuo. Water is added, then the mixture is extracted with EtOAc. The organic layer is washed with sat. aqueous NaCl solution, dried with MgSO4, and concentrated under reduced pressure. The crude product is recrystallized from EtOAc giving the title compound; [M+H]+=312; 1H-NMR (400 MHz, CDCl3): δ 12.90 (s, 1H), 9.47 (d, 1H), 8.86 (d, 1H), 8.70-8.64 (m, 2H), 7.84 (t, 1H), 7.45 (m, 1H), 7.33 (d, 1H), 6.84 (d, 1H), 3.22 (s, 1H), 2.74 (s, 3H).

Workup

  1. customthe solvent is removed in vacuo
  2. additionWater is added
  3. extractionthe mixture is extracted with EtOAc
  4. washThe organic layer is washed with sat. aqueous NaCl solution
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product is recrystallized from EtOAc giving the title compound

Sources & evidence

ORD record
ord-442160b774ce492cba00080caaa33256
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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