Water → 2-(azidomethyl)-6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4(3H)-one

HRID 241074Notes

Reaction equation

HRID 241074 reaction equation
Cl[CH2:2][C:3]1[NH:12][C:11](=[O:13])[C:10]2[CH2:9][C:8]([CH3:15])([CH3:14])[CH2:7][CH2:6][C:5]=2[N:4]=1.[N-:16]=[N+:17]=[N-:18].[Na+].O>CN(C=O)C>[N:16]([CH2:2][C:3]1[NH:12][C:11](=[O:13])[C:10]2[CH2:9][C:8]([CH3:15])([CH3:14])[CH2:7][CH2:6][C:5]=2[N:4]=1)=[N+:17]=[N-:18]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 1363315372-(Chloromethyl)-6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-ol

Product 1

HCID 1363315422-(azidomethyl)-6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4(3H)-oneYield 98.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(chloromethyl)-6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4(3H)-one (150 mg, 0.66 mmol, reagent preparation 17) in DMF (3 mL) was added sodium azide (215 mg, 3.3 mmol). The resulting mixture was stirred at rt for 35 min. Water was added and the resulting mixture was extracted twice with ethyl acetate. The combined organic extracts were washed with aqueous lithium chloride (10%), dried over magnesium sulfate, filtered, and concentrated in vacuo to provide 2-(azidomethyl)-6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4(3H)-one (151 mg, 0.65 mmol, 98% yield) as a waxy yellow solid. 1H NMR (400 MHz, CDCl3) δ 11.70 (br s, 1H), 4.41 (s, 2H), 2.66 (t, 2H), 2.33 (s, 2H), 1.58 (t, 3H), 1.00 (s, 6H); MS (EI) for C11H15N5O: 234 (MH+).

Workup

  1. extractionthe resulting mixture was extracted twice with ethyl acetate
  2. washThe combined organic extracts were washed with aqueous lithium chloride (10%)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8043024a4e5d42ba889ea0e77cd455da
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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