Methyl iodide → 4-Chloro-7-(methoxymethyl)-5,6,7,8-tetrahydroquinazoline

HRID 241073Notes

Reaction equation

HRID 241073 reaction equation
[Cl:1][C:2]1[C:11]2[CH2:10][CH2:9][CH:8]([CH2:12][OH:13])[CH2:7][C:6]=2[N:5]=[CH:4][N:3]=1.[C:14](=O)([O-])[O-].[K+].[K+].IC>C1COCC1>[Cl:1][C:2]1[C:11]2[CH2:10][CH2:9][CH:8]([CH2:12][O:13][CH3:14])[CH2:7][C:6]=2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86647826HCID 86647826, compound

Product 1

HCID 866478304-Chloro-7-(methoxymethyl)-5,6,7,8-tetrahydroquinazolineYield 35.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of (4-chloro-5,6,7,8-tetrahydroquinazolin-7-yl)methanol (reagent preparation 42, 0.80 g, 0.40 mmol), potassium carbonate (0.11 g, 0.81 mmol) and THF (15 mL) was added iodomethane (0.09 mL, 0.60 mmol). The reaction mixture was stirred for 18 hours and then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by silica gel chromatography provided 4-chloro-7-(methoxymethyl)-5,6,7,8-tetrahydroquinazoline (0.03 g, 35% yield) as a waxy solid. MS (ES) for C10H13ClN2O: 213 (MH+).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-154cbfcce2f5450fb4e66c8996722d02
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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