Water → Diethyl 4-(6-bromo-4-methylthioquinazolin-2-yl)benzyl(thio)phosphonate

HRID 54901Notes

Reaction equation

HRID 54901 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:27]=[CH:26][C:15]([CH2:16][S:17][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])=[CH:14][CH:13]=1)[N:6]=[C:5]2[SH:28].[CH2:29](N(CC)CC)C.CI.O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:27]=[CH:26][C:15]([CH2:16][S:17][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])=[CH:14][CH:13]=1)[N:6]=[C:5]2[S:28][CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 8471TriethylamineHCID 178476990HCID 178476990, compound

Product 1

HCID 70268853Diethyl 4-(6-bromo-4-methylthioquinazolin-2-yl)benzyl(thio)phosphonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 0.60 g quantity of the compound obtained in Example 52 was dissolved in 10 ml of THF, and 0.2 ml of triethylamine and 0.1 ml of methyl iodide were serially added thereto with stirring at room temperature. The stirring was continued at room temperature for 30 minutes. After adding 30 ml of water, the reaction mixture was extracted with chloroform. The chloroform layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform: n-hexane=2:1) and recrystallized from diethyl ether-n-hexane to provide 0.43 g of the objective compound as yellow crystals (melting point: 126°-127° C.).

Workup

  1. extractionthe reaction mixture was extracted with chloroform
  2. washThe chloroform layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: chloroform: n-hexane=2:1)
  6. customrecrystallized from diethyl ether-n-hexane

Sources & evidence

ORD record
ord-7149b49a825343869281f342268317c1
Source dataset
uspto-grants-1997_04
Patent number
US05624918

Reaction notes

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