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 395277Notes

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-d7d40e7b2ac149ce847a278623620f2c
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06605601B2

Reaction notes

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