2-Amino-2-methyl-1-propanol → HCID 135730640, compound

Participants

Reaction Steps

6-Isobutoxy-5-(2-methyl-7-oxo-3-propyl-6,7-dihydro-2H-pyrazolo[4,3-d]pyrimidin-5-yl)nicotinic acid (Example 24) (200 mg, 0.52 mmol) was dissolved in dichloromethane and oxalyl chloride (0.18 mL, 2.8 mmol) was added followed by 1 drop of N,N-dimethylformamide. The mixture was stirred for 2 h and the solvent was then removed in vacuo, azeotroping with further dichloromethane. A dichloromethane solution of the acid chloride was then added to a solution of 2-amino-2-methyl-1-propanol (0.05 mL, 0.52 mmol) and diisopropylethylamine (0.09 mL, 0.62 mmol) in dichloromethane and the mixture stirred for 2 h. The reaction mixture was diluted with further dichloromethane and washed with a 1 N solution of citric acid, followed by brine. The organics were dried (MgSO4) and concentrated in vacuo. The residue was redissolved in dichloromethane and thionyl chloride (0.05 mL, 0.62 mmol) was added. After 2 h the solution was washed with water then sodium bicarbonate solution. The organic phase was dried and concentrated. The crude residue was purified by flash column chromatography (50% ethyl acetate:pentane as eluant) to give the product.

Provenance & Evidence