Phenylacetylene → HCID 54236800, compound

HRID 1195802Notes

Reaction equation

C1(C#C)C=CC=CC=1.[CH3:9][Si:10]([C:13]#[CH:14])([CH3:12])[CH3:11].[Si]([O:22][CH2:23][CH2:24][O:25][CH2:26][N:27]1[C:35](I)=[C:33]([CH3:34])[C:31](=[O:32])[NH:30][C:28]1=[O:29])(C(C)(C)C)(C)C>>[OH:22][CH2:23][CH2:24][O:25][CH2:26][N:27]1[C:35]([C:14]#[C:13][Si:10]([CH3:12])([CH3:11])[CH3:9])=[C:33]([CH3:34])[C:31](=[O:32])[NH:30][C:28]1=[O:29]

Participants

Reactant 3

HCID 10821Phenylacetylene

HCID 66111Trimethylsilylacetylene

HCID 14477878HCID 14477878, compound

Product 1

HCID 54236800HCID 54236800, compound

Procedure

In place of phenylacetylene in Example 38 (2), 0.82 ml (6 mmol) of trimethylsilylacetylene was used to react with 880 mg (2 mmol) of 1-[(2-t-butyldimethylsilyloxyethoxy)methyl]-6-iodothymine for producing 1-[(2-hydroxyethoxy)methyl]-6-(2-trimethylsilylethynyl)thymine in the same manner as Example 38 (2). The obtained compound was dissolved in 100ml of methanol, was added to 1 ml of 1N sodium hydroxide aqueous solution and allowed to react for two minutes at room temperature. Then the reaction solution was neutralized with hydrochloric acid and concentrated. The resultant was distributed between ethyl acetate and aqueous layers, and the ethyl acetate layer then concentrated to dryness. The residue was crystallized from toluene/ethanol to obtain 170 mg of the target compound (Yield: 38%).

Sources & evidence

ORD record: ord-bedf277f409c4f099ecbcfeba83ad785
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05112835

Reaction notes

Loading…