1,6-Diazaspiro[3.5]nonane-1-propanenitrile, 3-methyl-β-oxo-6-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)- synthesis

Yield:-

Steps:

Multi-step reaction with 8 steps
1.1: triethylamine; diphenyl phosphoryl azide / toluene / 2.92 h / Reflux
1.2: 33 h / Reflux
2.1: ozone / chloroform; methanol / 0.5 h / -78 °C
2.2: 20 °C
3.1: hydrogen / palladium 10% on activated carbon / methanol / 1.5 h / 20 °C
4.1: carbon tetrabromide; triethylamine; triphenylphosphine / dichloromethane / 1 h / 0 - 20 °C
4.2: 0.67 h / 4 - 20 °C
5.1: trifluoroacetic acid / chloroform / 2 h / 4 - 20 °C
5.2: 4 °C / pH 9 - 10
6.1: potassium carbonate / water / 4 h / Reflux
7.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran; methanol / 3040.2 Torr
8.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 3 h / 100 °C

References:

US2011/136778,2011,A1