Bicarbonate Ion → HCID 178476611, compound

Participants

Reaction Steps

N,O-bis(trimethylsilyl)acetamide (29.6 g, 35 ml) was added to a stirred slurry of (3) (30 g, 58.8 mmol) and 2-amino-6-chloropurine (12 g, 70 mmol) in 1,2-dichloroethane (dried over sieves, 450 ml) and the mixture was refluxed for 40 min. to give a homogenous solution. The mixture was then removed from the heat and trimethylsilyltriflat (22 ml, 118 mmol) was added dropwise. The reaction mixture was refluxed for another 2 h. The reaction mixture was cooled to room temperature and a saturated aqueous solution of bicarbonate (400 ml) was added. The slurry was allowed to stir for 15 min, pH was adjusted to 7-8 using glacial acetic acid and the mixture was extracted with chloroform. The aqueous phase was extracted with AcOEt and chloroform and the organic phases were combined. The organic phase was washed with brine (2×250 ml) and bicarbonate (2×250 ml). The organic phase was dried over sodium sulfate and concentrated under reduced pressure to give compound (4) as a yellowish foam which expands during vacuum dessication

Provenance & Evidence