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4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo(2.2.2]oct-1-yl ester

HRID 480117
Notes
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Reaction equation

HRID 480117 reaction equation
[OH:1][C:2]12[CH2:9][CH2:8][C:5]([C:10]3[NH:18][C:17]4[C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH3:22])[C:14](=[O:23])[N:13]([CH2:24][CH2:25][CH3:26])[C:12]=4[N:11]=3)([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.CCN(CC)CC.[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1>C(Cl)Cl.CCOC(C)=O>[O:23]=[C:14]1[N:13]([CH2:24][CH2:25][CH3:26])[C:12]2[N:11]=[C:10]([C:5]34[CH2:8][CH2:9][C:2]([O:1][S:40]([C:37]5[CH:38]=[CH:39][C:34]([CH3:44])=[CH:35][CH:36]=5)(=[O:42])=[O:41])([CH2:7][CH2:6]3)[CH2:3][CH2:4]4)[NH:18][C:17]=2[C:16](=[O:19])[N:15]1[CH2:20][CH2:21][CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 99507768-(4-hydroxybicyclo[2.2.2]octan-1-yl)-1,3-dipropyl-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 86591740Toluene-4-sulfonic acid 4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo(2.2.2]oct-1-yl esterYield 54.1%

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 100 mg of 8-(4-Hydroxy-bicyclo[2.2.2]oct-1-yl)-1,3-dipropyl-3,7-dihydro-purin-2,6-dione (Example 13a) (0.28 mmol) in CH2Cl2 (10 ml) was added 40 μL of Et3N and the reaction mixture cooled in an ice bath. To this was added 100 mg of p-toluenesulfonyl chloride (0.52 mmol) and the reaction kept at 10° C. overnight. The reaction mixture was conc'd in vacuo and the residue taken up in EtOAc and washed 2× with dilute HCl (10 ml). The organic layer was dried over NaSO4 and conc'd. The residue was triturated in acetonitrile to afford 78 mg (54%) of pure white solid (MH+=515.10).

Workup

  1. temperaturethe reaction mixture cooled in an ice bath
  2. washwashed 2× with dilute HCl (10 ml)
  3. dry with materialThe organic layer was dried over NaSO4 and conc'd
  4. customThe residue was triturated in acetonitrile

Sources & evidence

ORD record
ord-1b13000334b249c5bbbab70c8a43cdf0
Source dataset
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06649600B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes