Ammonia → N2 (3-methoxyphenylacetyl)-2'-deoxyguanosine

Participants

Reaction Conditions

Reaction Steps

To dry 2'-deoxyguanosine (1) (14.2 g, 50 mmoles) in 300 ml of dry pyridine at 0° C. was added trimethylsilyl chloride (33 ml, 250 mmoles) and the mixture stirred at 0° C. for 1 hour. 3-Methoxyphenylacetyl chloride (40 ml, 250 mmoles) was added and the solution maintained at room temperature for 15 hours. The reaction mixture was then cooled in an ice bath and 50 ml of cold water was added. After 30 minutes, 50 ml of 29% aqueous ammonia was added and the mixture stirred for 30 minutes. The solution was then evaporated to near dryness and the residue dissolved in 400 ml water and 400 ml methylene chloride in a separating funnel. The product crystallized out of the aqueous solution upon extraction with CH2Cl2 was filtered off, washed with CH2Cl2 (3×50 ml) and ether (3×50 ml) and air dried to yield 15.56 g (75%) of N2 -(3-methoxyphenylacetyl)-2'-deoxyguanosine (2b), as confirmed by spectroscopic and elemental analysis.

Provenance & Evidence