Toluene → HCID 71557565, compound

5-tert-butyl-7-chloro-3-(2-chlorobenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine (10 g, 29.7 mmol, Eq: 1.00) was dissolved in Acetonitrile (54.6 g, 70.0 ml). N-Ethyldiisopropylamin (7.84 g, 10.3 ml, 59.5 mmol, Eq: 2) was added dropwise over 5-10 min. After 10 min at RT, a solution of (S)-pyrrolidin-3-ol (2.94 g, 2.8 ml, 32.7 mmol, Eq: 1.1) in Acetonitrile (2.27 g, 2.91 ml) added dropwise over 30 min at 20° C. After 2 h 30 reaction, toluene (86.5 g, 100 ml) was added and the reaction mixture was concentrated under reduced pressure to remove most of the acetonitrile. A 10% aqueous citric acid solution (100 ml) was added. The aqueous phase was separated and extracted with toluene (86.5 g, 100 ml). The organic phases were washed sequentially with half saturated aqueous NaHCO3 (50 ml) and half saturated aqueous NaCl (50 ml). The organic phases were combined dried over MgSO4 and rotavaped at 45° C./10 mbar. The crude product was taken up in ethanol (150 ml) and concentrated under reduced pressure. This was repeated twice in order to remove toluene and gave 11.1 g of the crude title compound as a light yellow solid/foam.

1. additionwas added
2. concentrationthe reaction mixture was concentrated under reduced pressure
3. customto remove most of the acetonitrile
4. additionA 10% aqueous citric acid solution (100 ml) was added
5. customThe aqueous phase was separated
6. extractionextracted with toluene (86.5 g, 100 ml)
7. washThe organic phases were washed sequentially with half saturated aqueous NaHCO3 (50 ml) and half saturated aqueous NaCl (50 ml)
8. dry with materialThe organic phases were combined dried over MgSO4
9. customrotavaped at 45° C.
10. concentrationconcentrated under reduced pressure
11. customto remove toluene

ORD record

ord-f1a5c3a612ef453a9bb1c1b07d2c24a5

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08741906B2