Phosphorus oxychloride → 4-Chloro-6-iodoquinazoline

HRID 571010Notes

Reaction equation

HRID 571010 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][NH:6][C:5]2=O.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([I:1])[CH:3]=2)[N:8]=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1354016666-Iodoquinazolin-4-one

Product 1

HCID 111738094-Chloro-6-iodoquinazoline

Procedure

6-Iodoquinazolin-4(3H)-one (10 g, 37 mmol) was refluxed in POCl3 (100 mL) overnight. Then POCl3 was removed in vacuo. The residue was dissolved in CH2Cl2 (500 mL). The organic phase was washed with water (100 mL) and dried (MgSO4). Then CH2Cl2 was removed in vacuo and 1404-174 was obtained (5.7 g, 53%): LC-MS: 291 [M+1]+, 1H NMR (CDCl3): δ 7.81 (d, J=9.0 Hz, 1 H), 8.21 (dd, J=9.0 Hz, J2=1.8 Hz, 1 H), 8.65 (d, J=1.8 Hz, 1 H), 9.06 (s, 1 H).

Workup

  1. customThen POCl3 was removed in vacuo
  2. dissolutionThe residue was dissolved in CH2Cl2 (500 mL)
  3. washThe organic phase was washed with water (100 mL)
  4. dry with materialdried (MgSO4)
  5. customThen CH2Cl2 was removed in vacuo
  6. custom1404-174 was obtained (5.7 g, 53%)

Sources & evidence

ORD record
ord-5faadc1de1484ee4ab14684ace05f7ca
Source dataset
uspto-grants-2015_05
Patent number
US09024024B2

Reaction notes

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