2-Morpholinoethanol → 1-(3-((tert-butyldimethylsilyl)oxy)propyl)-7-(4-chlorobenzyl)-3-methyl-8-(2-morpholinoethoxy)-1H-purine-2,6(3H,7H)-dione

HRID 2200739Notes

Reaction equation

HRID 2200739 reaction equation
[Na].Br[C:3]1[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:10]2[C:9](=[O:20])[N:8]([CH2:21][CH2:22][CH2:23][O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[C:7](=[O:32])[N:6]([CH3:33])[C:5]=2[N:4]=1.[O:34]1[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][OH:42])[CH2:36][CH2:35]1>O>[Si:25]([O:24][CH2:23][CH2:22][CH2:21][N:8]1[C:9](=[O:20])[C:10]2[N:11]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[C:3]([O:42][CH2:41][CH2:40][N:37]3[CH2:38][CH2:39][O:34][CH2:35][CH2:36]3)=[N:4][C:5]=2[N:6]([CH3:33])[C:7]1=[O:32])([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 611632-MorpholinoethanolHCID 5360545SodiumHCID 904028568-bromo-1-(3-((tert-butyldimethylsilyl)oxy)propyl)-7-(4-chlorobenzyl)-3-methyl-3,7-dihydro-1H-purine-2,6-dione2×

Product 1

HCID 904025871-(3-((tert-butyldimethylsilyl)oxy)propyl)-7-(4-chlorobenzyl)-3-methyl-8-(2-morpholinoethoxy)-1H-purine-2,6(3H,7H)-dioneYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Step 1 Sodium (0.053 g, 2.31 mmol) was dissolved in 2-morpholinoethanol (5 mL) and 8-bromo-1-(3-((tert-butyldimethylsilyl)oxy)propyl)-7-(4-chlorobenzyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (0.25 g, 0.46 mmol, intermediate 77) was added. The reaction was stirred at room temperature for 24 h. The reaction was diluted with water (75 mL) and extracted with ethyl acetate (3×75 mL). The combined extracts were dried with magnesium sulfate, filtered and the solvent was removed under reduced pressure to give 1-(3-((tert-butyldimethylsilyl)oxy)propyl)-7-(4-chlorobenzyl)-3-methyl-8-(2-morpholinoethoxy)-1H-purine-2,6(3H,7H)-dione (0.27 g, 100% yield) as a clear oil. LCMS retention time=2.990 min and 96% purity, LCMS MH+ 592.

Workup

  1. extractionextracted with ethyl acetate (3×75 mL)
  2. dry with materialThe combined extracts were dried with magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-26dbd29216ba4730bd48300e6cd6fa1f
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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