Water → HCID 89423187, Verbindung

To a solution of N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)methane sulfonamide (0.875 g, 4.18 mmol) in DMF (25 mL) was added 60% NaH in mineral oil (0.193 g, 4.83 mmol). After 10 minutes, methyl 2,6-dichloropyrimidine-4-carboxylate (0.871 g, 4.21 mmol) was added. After stirring for 30 minutes, the reaction mixture was diluted into 100 mL water and extracted three times with 50 mL EtOAc. The combined organic layers were washed once with 25 mL brine, dried over MgSO4, filtered, and evaporated to a residue. The residue was chromatographed over silica gel with 30-60% EtOAc in hexanes. The product fractions were concentrated in vacuo. After sitting overnight a crystalline solid formed. The solid was decanted and dried under vacuum to give methyl 2-chloro-6-(N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)methylsulfonamido)pyrimidine-4-carboxylate as a cream-colored powder (0.911 g, 2.40 mmol, 57% yield). LC/MS: m/z=380.2 [M+H]+.

1. extractionextracted three times with 50 mL EtOAc
2. washThe combined organic layers were washed once with 25 mL brine
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. customevaporated to a residue
6. customThe residue was chromatographed over silica gel with 30-60% EtOAc in hexanes
7. concentrationThe product fractions were concentrated in vacuo
8. waitAfter sitting overnight
9. customa crystalline solid formed
10. customThe solid was decanted
11. customdried under vacuum

ORD-Eintrag

ord-bc7adf33f4ba479694910e2d248892d6

Quelldatensatz

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09163008B2