Methanol → HCID 19087823, compound

HRID 1464339Notes

Reaction equation

HRID 1464339 reaction equation
[Na].[CH2:2]([C:6]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[N:33]([CH2:34][O:35][CH3:36])[N:32]=[N:31][N:30]=3)=[CH:19][CH:18]=2)[C:14](=[O:37])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:38])[CH:12]=2)[N:7]=1)[CH2:3][CH2:4][CH3:5].[CH3:39]O>C1COCC1>[CH2:2]([C:6]1[N:15]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[N:33]([CH2:34][O:35][CH3:36])[N:32]=[N:31][N:30]=3)=[CH:21][CH:22]=2)[C:14](=[O:37])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:38][CH3:39])[CH:12]=2)[N:7]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 887Methanol2×HCID 5360545SodiumHCID 19087859HCID 19087859, compound

Product 1

HCID 19087823HCID 19087823, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of sodium (28 mg) in methanol (3 ml) was added a solution of 2-butyl-6-hydroxy-3-[[2'-(N-methoxymethyltetrazol-5-yl)biphenyl-4-yl]methyl]-4(3H)-quinazolinone (0.6 g) in methanol (5 ml) and THF (5 ml) at 0° C. The solution was stirred at room temperature for 1 hour and evaporated to dryness. The residue was dissolved in DMF (5 ml) and methyl iodide (0.15 ml) was added to the solution. The mixture was stirred at room temperature for 17 hours, poured into water and extracted with ethyl acetate. The extract was washed with water, dried and evaporated to dryness. The residue was purified by column chromatography on silica gel to give a crystalline product. Recrystallization from ether-hexane gave colorless crystals (0.48 g, 78%).

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in DMF (5 ml)
  3. additionmethyl iodide (0.15 ml) was added to the solution
  4. stirringThe mixture was stirred at room temperature for 17 hours
  5. additionpoured into water
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with water
  8. customdried
  9. customevaporated to dryness
  10. customThe residue was purified by column chromatography on silica gel
  11. customto give a crystalline product
  12. customRecrystallization from ether-hexane

Sources & evidence

ORD record
ord-3734aac1c73e48dca07f218b7cef9f00
Source dataset
uspto-grants-1994_04
Patent number
US05304565

Reaction notes

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