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2-Amino-1-butanol, (-)- → 3-{4-[6-(1-Hydroxymethyl-propylamino)-2-oxo-3-propyl-3,7-dihydro2H-purin-8-yl]-bicyclo[2.2.2]oct-1-yl]-propionic acid methyl ester

HRID 395286
Notes
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Reaction equation

HRID 395286 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][CH2:5][C:6]12[CH2:13][CH2:12][C:9]([C:14]3[NH:22][C:21]4[C:20](SC)=[N:19][C:18](=[O:25])[N:17]([CH2:26][CH2:27][CH3:28])[C:16]=4[N:15]=3)([CH2:10][CH2:11]1)[CH2:8][CH2:7]2.[NH2:30][C@H:31]([CH2:34][CH3:35])[CH2:32][OH:33]>CS(C)=O>[CH3:1][O:2][C:3](=[O:29])[CH2:4][CH2:5][C:6]12[CH2:13][CH2:12][C:9]([C:14]3[NH:22][C:21]4[C:20]([NH:30][CH:31]([CH2:32][OH:33])[CH2:34][CH3:35])=[N:19][C:18](=[O:25])[N:17]([CH2:26][CH2:27][CH3:28])[C:16]=4[N:15]=3)([CH2:10][CH2:11]1)[CH2:8][CH2:7]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 27238562-Amino-1-butanol, (-)-2×HCID 119944193-[4-(6-Methylsulfanyl-2-oxo-3-propyl-3,7-dihydro-2H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-propionic acid methyl ester

Product 1

HCID 691473133-{4-[6-(1-Hydroxymethyl-propylamino)-2-oxo-3-propyl-3,7-dihydro2H-purin-8-yl]-bicyclo[2.2.2]oct-1-yl]-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

3-[4-(6-Methylsulfanyl-2-oxo-3-propyl-3,7-dihydro-2H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-propionic acid methyl ester (105 mg) was dissolved in 2 mL of DMSO along with an appropriate amino alcohol (e.g., 160 uL of (R)-2-amino-1-butanol for compound 3). The reaction mixture was stirred at 150° C. for 3 h. It was then cooled to rt and purified by preparative HPLC to afford 50 mg of the titled compound.

Workup

  1. temperatureIt was then cooled to rt
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-3b1a20925d52485ea1984b3f68fa6f91
Source dataset
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06605601B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes