Isopropyl iodide → HCID 20434880, compound

HRID 1154313Notes

Reaction equation

HRID 1154313 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[CH2:20][CH2:19][CH:18]([CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][NH:24][S:23]2(=[O:29])=[O:28])[CH2:17][CH2:16]1.[H-].[Na+].[CH:32](I)([CH3:34])[CH3:33]>CN(C)C=O>[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[CH2:16][CH2:17][CH:18]([CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][N:24]([CH:32]([CH3:34])[CH3:33])[S:23]2(=[O:28])=[O:29])[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 20434888HCID 20434888, compound

Product 1

HCID 20434880HCID 20434880, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 1-(6,7-dimethoxyquinazolin-4-yl)-4-[(1,1-dioxotetrahydro-1,2,6-thiadiazin-2-yl)methyl]piperidine 1/2 CH3CH2OCOCH3 (0.7 g) (prepared as in Example 9) in dimethylformamide (4.0 cm3) was treated at room temperature with sodium hydride (100 mg. of a 50% dispersion in oil) and the mixture was stirred for 45 minutes. Isopropyl iodide (255 mg) was then added and the resulting mixture was stirred for 6 hours. The solvent was removed in vacuo and the residue was taken into chloroform (50 cm3) and water (25 cm3). The aqueous phase was extracted with chloroform (2×20 cm3) and the dried (MgSO4) extracts were evaporated to yield an oil which was chromatographed on silica (Merck 60.9385) eluting with chloroform to give a gum. Crystallisation from ethyl acetate afforded 1-(6,7-dimethoxyquinazolin-4-yl)-4-([1,1-dioxo-6-isopropyltetrahydro-1,2,6-thiadiazin-2-yl]methyl)piperidine, m.p. 158°-161° (460 mg).

Workup

  1. stirringthe resulting mixture was stirred for 6 hours
  2. customThe solvent was removed in vacuo
  3. extractionThe aqueous phase was extracted with chloroform (2×20 cm3)
  4. dry with materialthe dried (MgSO4) extracts
  5. customwere evaporated
  6. customto yield an oil which
  7. customwas chromatographed on silica (Merck 60.9385)
  8. washeluting with chloroform
  9. customto give a gum
  10. customCrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-4cfbbe9b8397425f9cf1240321102095
Source dataset
uspto-grants-1984_12
Patent number
US04489075

Reaction notes

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