Dimethyl Sulfate → 1H-Purine-2,6-dione, 3,7-dihydro-8-(2-(1,1'-biphenyl)-4-ylethenyl)-1,3-diethyl-7-methyl-, (E)-

HRID 1077527Notes

Reaction equation

HRID 1077527 reaction equation
[CH2:1]([N:3]1[C:12](=[O:13])[C:11]2[NH:10][C:9](/[CH:14]=[CH:15]/[C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:18][CH:17]=3)=[N:8][C:7]=2[N:6]([CH2:28][CH3:29])[C:4]1=[O:5])[CH3:2].[OH-].[Na+].S(OC)(O[CH3:36])(=O)=O>O.CO>[CH2:1]([N:3]1[C:12](=[O:13])[C:11]2[N:10]([CH3:36])[C:9](/[CH:14]=[CH:15]/[C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:18][CH:17]=3)=[N:8][C:7]=2[N:6]([CH2:28][CH3:29])[C:4]1=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 64489391H-Purine-2,6-dione, 3,7-dihydro-8-(2-(1,1'-biphenyl)-4-ylethenyl)-1,3-diethyl-, (E)-

Product 1

HCID 64489401H-Purine-2,6-dione, 3,7-dihydro-8-(2-(1,1'-biphenyl)-4-ylethenyl)-1,3-diethyl-7-methyl-, (E)-Yield 30.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Compound 170 (1.50 g, 3.89 mmol) obtained in Reference Example 167 was suspended in a mixed solvent of 13 ml of water, 3.9 ml of a 2N aqueous solution of sodium hydroxide, and 7 ml of methanol. To the suspension was dropwise added 0.55 ml (5.83 mmol) of dimethyl sulfate, and the resultant mixture was stirred at 60° C. for 4 hours. Water (10 ml) was added thereto, and the deposited crystals were collected by filtration and dried. The obtained crude crystals were purified by silica gel column chromatography, followed by recrystallization from ethyl acetate to give 480 mg (yield 28%) of Compound 171 as yellow columns.

Workup

  1. filtrationthe deposited crystals were collected by filtration
  2. customdried
  3. customThe obtained crude crystals
  4. customwere purified by silica gel column chromatography
  5. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-a367863ddae04dc9b33e25742fe01104
Source dataset
uspto-grants-1996_08
Patent number
US05543415

Reaction notes

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