HCID 86667430, compound → (1R,3S)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)-1-(methylthiomethyl)cyclohexanol

2-chloro-5-fluoro-N-((3R,5S)-1-oxaspiro[2.5]octan-5-yl)pyrimidin-4-amine, 49b, (0.10 g, 0.38 mmol) was dissolved in THF (2 mL). Methylsulfanylsodium (0.08 g, 1.15 mmol) was added to the reaction and the mixture was allowed to stir at room temperature for 3 hrs. An additional 36 mg portion of methylsulfanylsodium in THF (2 mL) was added and the reaction mixture was stirred overnight at room temperature. After LCMS showed starting material was still present, the reaction was warmed to 50° C. and stirred for 1 hr. The reaction was quenched with water and diluted with EtOAc. The layers were separated and the organic phase was washed with brine, dried (MgSO4), filtered and evaporated to dryness. The crude residue was purified via silica gel chromatography (0-100% Etoac/hexanes gradient). The product (contaminated with small amount of staring material) was carried on to the next step without further purification. LCMS RT=3.56 (M+1) 306.2.

1. stirringthe reaction mixture was stirred overnight at room temperature
2. temperaturethe reaction was warmed to 50° C.
3. stirringstirred for 1 hr
4. customThe reaction was quenched with water
5. additiondiluted with EtOAc
6. customThe layers were separated
7. washthe organic phase was washed with brine
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. customevaporated to dryness
11. customThe crude residue was purified via silica gel chromatography (0-100% Etoac/hexanes gradient)
12. customThe product (contaminated with small amount of staring material) was carried on to the next step without further purification
13. customLCMS RT=3.56 (M+1) 306.2

ORD record

ord-b0e6d08b02d049c4bb51c9213c26bd8b

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09345708B2