Phosphorus oxychloride → 2-(Azidomethyl)-4-chloro-6,6-dimethyl-5,6,7,8-tetrahydroquinazoline

HRID 241075Notes

Reaction equation

HRID 241075 reaction equation
[N:1]([CH2:4][C:5]1[NH:14][C:13](=O)[C:12]2[CH2:11][C:10]([CH3:17])([CH3:16])[CH2:9][CH2:8][C:7]=2[N:6]=1)=[N+:2]=[N-:3].P(Cl)(Cl)([Cl:20])=O>C(Cl)(Cl)Cl>[N:1]([CH2:4][C:5]1[N:14]=[C:13]([Cl:20])[C:12]2[CH2:11][C:10]([CH3:17])([CH3:16])[CH2:9][CH2:8][C:7]=2[N:6]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1363315422-(azidomethyl)-6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4(3H)-one

Product 1

HCID 866478322-(Azidomethyl)-4-chloro-6,6-dimethyl-5,6,7,8-tetrahydroquinazolineYield 83%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-(azidomethyl)-6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4(3H)-one (151 mg, 0.65 mmol) in chloroform (1.2 mL) was treated with phosphorus oxychloride (600 uL) at 60° C. for 1 h 20 min. After cooling to rt, the volatile materials were removed in vacuo, and the resulting residue was dissolved in ethyl acetate. The organic solution was washed with saturated aqueous sodium bicarbonate, and the aqueous phase was back extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to provide 2-(azidomethyl)-4-chloro-6,6-dimethyl-5,6,7,8-tetrahydroquinazoline (136 mg, 0.54 mmol, 83% yield) as an orange oil. 1H NMR (400 MHz, CDCl3) δ 4.47 (s, 2H), 2.94 (t, 2H), 2.55 (s, 2H), 1.68 (t, 2H), 1.05 (s, 6H); MS (EI) for C11H14ClN5: 252 (MH+).

Workup

  1. customthe volatile materials were removed in vacuo
  2. dissolutionthe resulting residue was dissolved in ethyl acetate
  3. washThe organic solution was washed with saturated aqueous sodium bicarbonate
  4. extractionthe aqueous phase was back extracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-93734e4b18454505b81595063847cb40
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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