Tetrabutylammonium Fluoride → HCID 18932737, compound

HRID 1597996Notes

Reaction equation

HRID 1597996 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:24]#[C:25][Si](C)(C)C)[CH:22]=2)[CH2:17][CH2:16]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CO.C1COCC1>[C:24]([C:21]1[CH:22]=[C:23]2[C:18]([CH2:17][CH2:16][N:15]2[C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][N:7]=2)=[CH:19][CH:20]=1)#[CH:25]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 18932772HCID 18932772, compound

Product 1

HCID 18932737HCID 18932737, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 6,7-dimethoxy-4-(6-trimethylsilanylethynyl-2,3-dihydro-indol-1-yl)-quinazoline (1 eq.; 50 mg; 0.124 mmol) in MeOH (2 mL)/THF (2 mL) was treated with 1M tetrabutylammonium fluoride (2 eq.; 0.248 mL) in THF at 20° C. for 16 hours. Solvents were removed in vacuo and the residue was dissolved in 1:1 EtOAc/Et2O washed with saturated aqueous NaHCO3, dried over Na2SO4(s), filtered and concentrated in vacuo. The product was converted to the HCl salt using a procedure analogous to that described for Example 2. (M.P. 241°-243° C.; LC-MS: 332 (MH+); RP18-HPLC RT: 4.48 min)

Workup

  1. customSolvents were removed in vacuo
  2. dissolutionthe residue was dissolved in 1:1 EtOAc/Et2O
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialdried over Na2SO4(s)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-862c151e61a64192867c1589ec3e5022
Source dataset
uspto-grants-1998_04
Patent number
US05736534

Reaction notes

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