Diisopropyl Ether → 4-Chloro-6-iodoquinazoline

HRID 1372484Notes

Reaction equation

HRID 1372484 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.C1(P(Cl)([Cl:21])=O)C=CC=CC=1.C(OC(C)C)(C)C>>[Cl:21][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

4

Reactant 3

HCID 7914Diisopropyl EtherHCID 69990Phenylphosphonic dichlorideHCID 1354016666-Iodoquinazolin-4-one2×

Product 1

HCID 111738094-Chloro-6-iodoquinazoline

Conditions

Temperature
150 °C

Procedure

A mixture of 6-iodoquinazolin-4(3H)-one (Intermediate 11, 100 mg, 0.37 mmol) and phenylphosphonic dichloride (1.5 mL) was heated at 150° C. for one h. After cooling the reaction mixture in an ice bath, isopropyl ether was added. The resultant crystalline precipitate was collected by filtration, and was then stirred with saturated aqueous sodium bicarbonate solution. The solution was extracted with three portions of ethyl acetate, and the combined extracts were dried (magnesium sulfate) and concentrated under reduced pressure to give the crude product. Purification by preparative thin layer chromatography (silica gel, 5% and 10% ethyl acetate/hexanes) afforded the desired product. LC/MS 291 (M+1).

Workup

  1. temperatureAfter cooling the reaction mixture in an ice bath
  2. filtrationThe resultant crystalline precipitate was collected by filtration
  3. extractionThe solution was extracted with three portions of ethyl acetate
  4. dry with materialthe combined extracts were dried (magnesium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product
  7. customPurification by preparative thin layer chromatography (silica gel, 5% and 10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f0438b6c22454b948d5f9be2cdb47125
Source dataset
uspto-grants-2007_01
Patent number
US07157490B2

Reaction notes

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