Methanol → 1-(2-Hydroxyethoxymethyl)-5-(3-trifluoroacetamido-1-propynyl)cytosine

HRID 1886514Notes

Reaction equation

HRID 1886514 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:13]=[C:12](I)[C:10]([NH2:11])=[N:9][C:7]1=[O:8].[CH2:15]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[C:16]#[CH:17].CO>ClCCl>[OH:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:13]=[C:12]([C:17]#[C:16][CH2:15][NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[C:10]([NH2:11])=[N:9][C:7]1=[O:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 110948052,2,2-trifluoro-N-(prop-2-yn-1-yl)acetamideHCID 199580071-(2-Hydroxyethoxymethyl)5-iodocytosine

Product 1

HCID 199580181-(2-Hydroxyethoxymethyl)-5-(3-trifluoroacetamido-1-propynyl)cytosineYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Iodide 68 (311 mg, 1.00 mmol) was coupled to N-propargyltrifluoroacetamide (43) according to the general procedure described in Example 1C. Flash chromatography on silica gel (3×20 cm) with 5%, 10% and 20% methanol in dichlormethane afforded alkynylamino nucleotide 69 as a pale yellow foam (77.4 mg, 23%).

Sources & evidence

ORD record
ord-62711a5c8293440989d1d6bf6f0c6241
Source dataset
uspto-grants-1992_09
Patent number
US05151507

Reaction notes

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