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Hydrochloric Acid → 8-(4-Hydroxymethyl-bicyclo[2.2.2]oct-1-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione

HRID 480109
Notes
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Reaction equation

HRID 480109 reaction equation
C[O:2][C:3]([C:5]12[CH2:12][CH2:11][C:8]([C:13]3[NH:21][C:20]4[C:19](=[O:22])[N:18]([CH2:23][CH2:24][CH3:25])[C:17](=[O:26])[N:16]([CH2:27][CH2:28][CH3:29])[C:15]=4[N:14]=3)([CH2:9][CH2:10]1)[CH2:7][CH2:6]2)=O.[Li+].[BH4-].CO.Cl>CCOC(C)=O.C1COCC1>[OH:2][CH2:3][C:5]12[CH2:10][CH2:9][C:8]([C:13]3[NH:21][C:20]4[C:19](=[O:22])[N:18]([CH2:23][CH2:24][CH3:25])[C:17](=[O:26])[N:16]([CH2:27][CH2:28][CH3:29])[C:15]=4[N:14]=3)([CH2:11][CH2:12]1)[CH2:7][CH2:6]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4148881Lithium borohydrideHCID 98440604-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester

Product 1

HCID 119956518-(4-Hydroxymethyl-bicyclo[2.2.2]oct-1-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dioneYield 88%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester (Example 14) (1.40 g, 3.48 mmol) was combined with LiBH4 (0.379 g, 17.4 mmol), MeOH (0.141 ml, 3.48 mmol), and 100 ml of THF and the resultant mixture was brought to reflux for 18 h. After cooling to rt, 50 ml of 1M HCl were added and the mixture conc'd in vacuo. The residue was dissolved in EtOAc and washed with 1M HCl, sat'd NaHCO3, brine, and dried over Na2SO4. The EtOAc solution was conc'd in vacuo to give 1.15 g (88% yield), of a white solid. (MH+=375.50)

Workup

  1. temperatureto reflux for 18 h
  2. washwashed with 1M HCl
  3. dry with materialdried over Na2SO4
  4. customto give 1.15 g (88% yield)

Sources & evidence

ORD record
ord-c22c7b9dab734a3c9a8e8a75648e6549
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