4-Chloro-6-iodoquinazoline → HCID 60162843, compound

HRID 1422993Notes

Reaction equation

HRID 1422993 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])[NH2:5].Cl[C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([I:29])[CH:27]=2)[N:22]=[CH:21][N:20]=1>C(O)(C)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([I:29])[CH:27]=3)[N:22]=[CH:21][N:20]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17]

Participants

4

Reactant 2

HCID 111738094-Chloro-6-iodoquinazolineHCID 219521053-Chloro-4-[(2-fluorophenyl)methoxy]aniline

Product 1

HCID 60162843HCID 60162843, compoundYield 197.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

In a glass flask provided with a condenser, thermometer, mechanical stirrer and nitrogen inlet, —under nitrogen flow—15.0 g of 3-chloro-4-[(2-fluorobenzyl)oxy]aniline of formula (IV), 17.49 g of 4-chloro-6-iodoquinazoline of formula (VIII) (available in the market), 300 mL of Isopropanol were introduced. The reaction mixture was stirred at 70° C. for 2 hrs. Upon completing the reaction cooling was carried out at ambient temperature. The formed yellow solid was filtered washing the solid with 20 mL of cold Isopropanol. 31.9 g of product equivalent to a 98.7% molar yield were obtained. 1H-NMR spectrum according to FIG. 5.

Workup

  1. customIn a glass flask provided with a condenser
  2. temperaturecooling
  3. customwas carried out at ambient temperature
  4. filtrationThe formed yellow solid was filtered
  5. washwashing the solid with 20 mL of cold Isopropanol

Sources & evidence

ORD record
ord-84c9dc1c902142b28c7d23fbabe3e3e8
Source dataset
uspto-grants-2015_01
Patent number
US08927558B2

Reaction notes

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