Uridine, 5'-amino-2',5'-dideoxy- → 5'-[(4-Cyanotrityl)amino]-2',5'-dideoxyuridine

HRID 1818668Notes

Reaction equation

[C:1]([C:3]1[CH:22]=[CH:21][C:6]([C:7](Cl)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)#[N:2].[NH2:23][CH2:24][C@H:25]1[O:29][C@@H:28]([N:30]2[CH:37]=[CH:36][C:34](=[O:35])[NH:33][C:31]2=[O:32])[CH2:27][C@@H:26]1[OH:38]>N1C=CC=CC=1>[C:1]([C:3]1[CH:22]=[CH:21][C:6]([C:7]([NH:23][CH2:24][C@H:25]2[O:29][C@@H:28]([N:30]3[CH:37]=[CH:36][C:34](=[O:35])[NH:33][C:31]3=[O:32])[CH2:27][C@@H:26]2[OH:38])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

Conditions

Temperature: 40 °C

Procedure

4-Cyanotrityl chloride (0.406 g, 1.34 mmol) was added to a solution of 5′-amino-2′,5′-dideoxyuridine (0.239 g, 1.05 mmol) in dry pyridine (5 mL). The reaction mixture was stirred at 40° C. for 48 h. The reaction mixture was filtered and the filtrate concentrated in vacuo. Purification was carried out using flash column chromatography eluting the column (ISOLUTE SI) with a gradient of 0→5% CH3OH in CHCl3. The fractions with Rf=0.31 (10% CH3OH/CHCl3) afforded the title compound as a white crystalline solid (0.386 g, 37%).

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate concentrated in vacuo
customPurification
washeluting the column (ISOLUTE SI) with a gradient of 0→5% CH3OH in CHCl3

Sources & evidence

ORD record: ord-30127ba28c504c3e99ca3739cf460a25
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601702B2

Reaction notes

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