Trimethylamine → HCID 10959042, compound

HRID 130310Notes

Reaction equation

[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[C@H:15]([OH:16])[C@H:14]([OH:17])[C@@H:13]([CH2:18][OH:19])[O:12]2)=[C:4](Cl)[N:3]=1.[CH:21]1([NH2:26])[CH2:25][CH2:24][CH2:23][CH2:22]1.CN(C)C>C(O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[C@H:15]([OH:16])[C@H:14]([OH:17])[C@@H:13]([CH2:18][OH:19])[O:12]2)=[C:4]([NH:26][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To suspension of (4S,2R,3R,5R)-2-[2-amino-6-chloro-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol in 15 mL of ethanol was added 0.4 g of cyclopentyl amine and 10 mmol of trimethyl amine. The mixture was stirred at 80° C. for 24 hours. The residue was purified using preparative thin layer chromatography (15:1 dichloromethane:methanol) to yield (4S,2R,3R,5R)-2-[2-amino-6-(cyclopentylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol, a compound of formula (8).

Workup

customThe residue was purified

Sources & evidence

ORD record: ord-dff332c8c27b47eca824a149021d7b14
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07381714B2

Reaction notes

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