2-Amino-1-butanol, (-)- → 8-(4-Hydroxy-bicyclo[2.2.2]oct-1-yl)-6-(1-hydroxymethyl-propylamino)-3-propyl-3,7-dihydro-purin-2-one

HRID 1793812Notes

Reaction equation

[OH:1][C:2]12[CH2:9][CH2:8][C:5]([C:10]3[NH:18][C:17]4[C:16](SC)=[N:15][C:14](=[O:21])[N:13]([CH2:22][CH2:23][CH3:24])[C:12]=4[N:11]=3)([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.[NH2:25][C@H:26]([CH2:29][CH3:30])[CH2:27][OH:28]>CS(C)=O>[OH:1][C:2]12[CH2:9][CH2:8][C:5]([C:10]3[NH:18][C:17]4[C:16]([NH:25][CH:26]([CH2:27][OH:28])[CH2:29][CH3:30])=[N:15][C:14](=[O:21])[N:13]([CH2:22][CH2:23][CH3:24])[C:12]=4[N:11]=3)([CH2:6][CH2:7]1)[CH2:4][CH2:3]2

Participants

Conditions

Temperature: 150 °C

Procedure

8-(4-Hydroxy-bicyclo[2.2.2]oct-1-yl)-6-methylsulfanyl-3-propyl-3,7-dihydro-purin-2-one (125 mg, 0.36 mmol) was dissolved in 3 mL of DMSO along with an excess of an appropriate amino alcohol (e.g., (R)-(−)-2-amino-1-butanol (0.24 mL, 7 eq) for compound 2). The resulting reaction mixture was stirred at 150° C. for 3 h. It was then cooled to rt and purified by preparative HPLC to afford 110 mg of the titled compound.

Workup

customThe resulting reaction mixture
temperatureIt was then cooled to rt
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-574b524d424143dd97c48a1e553e053c
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022686B2

Reaction notes

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