Thiophenol → HCID 178433338, compound

A solution of (E)-ethyl 3-(2-amino-4-(cis-4-(2-hydroxyethoxy)cyclohexylamino)-6-methylpyrimidin-5-yl)acrylate (615 mg, 1.69 mmol), thiophenol (173 ul, 1.69 mmol), benzenethiol, sodium salt (248 mg, 1.69 mmol), 1,5-diazabicyclo5,4,0)undec-5-ene (1.01 mL, 6.75 mmol) and diisopropylethyl amine (1.76 mL, 10.1 mmol) in N′,N-dimethylformamide (11.2 mL) was heated to 120° C. overnight. The reaction mixture was concentrated and the residue was partitioned between methyl tert-butylether (500 mL) and saturated sodium bicarbonate (50 mL). The organic layer was separated and washed with 50% brine, dried (Na2SO4), filtered and concentrated. The combined aqueous layers were extracted with chloroform (3×175 mL). Combined extracts were washed with brine (50 mL), dried (Na2SO4), filtered and concentrated. The crude product was purified by flash chromatography eluting with chloroform/7N ammonia in methanol (0-6%) to afford the title compound (411 mg, 77%).

1. concentrationThe reaction mixture was concentrated
2. customthe residue was partitioned between methyl tert-butylether (500 mL) and saturated sodium bicarbonate (50 mL)
3. customThe organic layer was separated
4. washwashed with 50% brine
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated
8. extractionThe combined aqueous layers were extracted with chloroform (3×175 mL)
9. washCombined extracts were washed with brine (50 mL)
10. dry with materialdried (Na2SO4)
11. filtrationfiltered
12. concentrationconcentrated
13. customThe crude product was purified by flash chromatography
14. washeluting with chloroform/7N ammonia in methanol (0-6%)

ORD record

ord-7fe3cae6ff43414e9692b626d04ed54e

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07696213B2