Tetrabutylammonium Fluoride → HCID 20434936, compound

HRID 1154314Notes

Reaction equation

HRID 1154314 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][NH:5][S:4](=[O:9])(=[O:8])[N:3]=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][C:21]=1[O:22][CH3:23])[N:18]=[CH:17][N:16]=[C:15]2[N:24]1[CH2:29][CH2:28][CH:27]([CH2:30]I)[CH2:26][CH2:25]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][C:21]=1[O:22][CH3:23])[N:18]=[CH:17][N:16]=[C:15]2[N:24]1[CH2:29][CH2:28][CH:27]([CH2:30][N:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[N:3][S:4]2(=[O:9])=[O:8])[CH2:26][CH2:25]1

Participants

4

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 204349324-[4-(Iodomethyl)piperidin-1-yl]-6,7-dimethoxyquinazolineHCID 178434802HCID 178434802, compound

Product 1

HCID 20434936HCID 20434936, compound

Procedure

A mixture of 3-methyl-6H-1,2,6-thiadiazine-1,1-dioxide (0.584 g) and 1-(6,7-dimethoxyquinazolin-4-yl)-4-iodomethylpiperidine (0.826 g) were heated under reflux with tetrabutylammonium fluoride (4 ml; 1.0M in tetrahydrofuran [T.H.F.]) for 24 hours. The solvent was then removed in vacuo and the residue was chromatographed on silica (Merck 60.9385) eluting with chloroform to give a foam. Crystallisation from ethyl acetate gave 1-(6,7-dimethoxyquinazolin-4-yl)-4-(1,1-dioxo-5-methyl-1,2,6-thiadiazin-2-yl)methylpiperidine as white needles, m.p. 203°-207°, (0.35 g).

Workup

  1. temperaturewere heated
  2. customThe solvent was then removed in vacuo
  3. customthe residue was chromatographed on silica (Merck 60.9385)
  4. washeluting with chloroform
  5. customto give a foam
  6. customCrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-f6e40673c1644acf80b405ace399bb87
Source dataset
uspto-grants-1984_12
Patent number
US04489075

Reaction notes

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