Dichloromethane → 8-Bromo-2-chloroquinazoline

HRID 1672469Notes

Reaction equation

HRID 1672469 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([Cl:12])[N:8]=[C:7]2N.N(OCCC(C)C)=O.CC(=O)OCC.C(Cl)Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([Cl:12])[N:8]=[CH:7]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8053Isoamyl NitriteHCID 8857Ethyl AcetateHCID 137858778-Bromo-2-chloroquinazolin-4-amine

Product 1

HCID 457900618-Bromo-2-chloroquinazolineYield 67.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 8-bromo-2-chloroquinazolin-4-amine (12.93 g, 50 mmol) in THF (500 mL) was added isoamyl nitrite (23.43 g, 200 mmol) over 3 hours and 40 mins at 60° C. The mixture was stirred for another 5 hours. TLC (PE:EA, 1:1) showed reaction complete. After cooling to room temperature, the solvent was stripped and the residue was taken into DCM (300 mL). The organic layer was washed with brine (100 mL), water (100 mL), then dried over anhydrous Na2SO4 and purified by chromatography (DCM:PE, 1:1) to give the title compound as a yellow solid (8.21 g, 67%). 1HNMR (DMSO-d6, 400 MHz): δ 9.66 (s, 1H), 8.45 (dd, J=0.8, 7.6 Hz, 1H), 8.26 (dd, J=0.8, 8.0 Hz, 7.73 (dd, J=7.6, 8.0 Hz, 1H).

Workup

  1. custom40 mins
  2. customat 60° C
  3. customreaction complete
  4. washThe organic layer was washed with brine (100 mL), water (100 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. custompurified by chromatography (DCM:PE, 1:1)

Sources & evidence

ORD record
ord-c761042b62864079a88a12fad225bcfb
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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