Methyl iodide → diethyl 4-(3-methyl-4(3H)-quinazolinon-2-yl)benzylphosphonate

HRID 482444Notes

Reaction equation

HRID 482444 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:26]=[CH:25][C:15]([CH2:16][P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])=[CH:14][CH:13]=2)[N:3]=1.[CH3:27]C(C)([O-])C.[K+].CI>CO>[CH3:27][N:3]1[C:2](=[O:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]1[C:12]1[CH:13]=[CH:14][C:15]([CH2:16][P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 178476844HCID 178476844, compound

Product 1

HCID 10643860diethyl 4-(3-methyl-4(3H)-quinazolinon-2-yl)benzylphosphonate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A 5.9 g quantity of diethyl 4-(4-hydroxyquinazolin-2-yl)benzylphosphonate, 1.8 g of potassium tert-butoxide and 2.3 g of methyl iodide were suspended in 100 ml of anhydrous methanol and stirred with heating at 40° C. for 16 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: methylene chloride: methanol=100:1) and the crude crystals thus obtained were recrystallized from methylene chloride-n-hexane to provide 3.0 g of the title compound as colorless crystals.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluent: methylene chloride: methanol=100:1)
  4. customthe crude crystals thus obtained
  5. customwere recrystallized from methylene chloride-n-hexane

Sources & evidence

ORD record
ord-1e960697b65048cf946b43a3a37e22a9
Source dataset
uspto-grants-1998_08
Patent number
US05798344

Reaction notes

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