Tetrabutylammonium Fluoride → 3-(1,3-Dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile

Temperature

60 °C

TBAF solution (20.3 mL, 20.3 mmol) was added to a suspension of 3-(1,3-dimethyl-2,4-dioxo-6-((2-(trimethylsilyl)ethoxy)methyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile (step 3) (832 mg, 2.0 mmol) in THF (6 mL), giving a solution which was stirred at 60° C. for 1 hour. Most of the organic solvent was removed from the reaction mixture, water (100 mL) was added and the mixture was stirred for 5 minutes The aqueous suspension was extracted with choroform (4×100 mL). A large amount of the mixture remained as an emulsion. Sat brine (100 mL) was added to break up the emulsion, and the aqueous phase was extracted with more chloroform (4×100 mL). The combined organic extracts were dried with magnesium sulfate and the solvent was removed under vacuum to yield a red oil. The crude red oil was triturated with methanol to give a pink solid which was dried under vacuum at 50° C. The solid was triturated with methanol again and dried under vacuum at 50° C.

1. customgiving a solution which
2. customMost of the organic solvent was removed from the reaction mixture, water (100 mL)
3. additionwas added
4. stirringthe mixture was stirred for 5 minutes The aqueous suspension
5. extractionwas extracted with choroform (4×100 mL)
6. additionSat brine (100 mL) was added
7. extractionthe aqueous phase was extracted with more chloroform (4×100 mL)
8. dry with materialThe combined organic extracts were dried with magnesium sulfate
9. customthe solvent was removed under vacuum
10. customto yield a red oil
11. customThe crude red oil was triturated with methanol
12. customto give a pink solid which
13. customwas dried under vacuum at 50° C
14. customThe solid was triturated with methanol again
15. customdried under vacuum at 50° C.

ORD record

ord-824bbdf5afee45be884f39d3949fd276

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359381B2