Water → HCID 89423187, compound

HRID 1752417Notes

Reaction equation

HRID 1752417 reaction equation
[CH3:1][C:2]1([CH3:13])[O:6][CH:5]([CH2:7][NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH2:4][O:3]1.[H-].[Na+].[Cl:16][C:17]1[N:22]=[C:21]([C:23]([O:25][CH3:26])=[O:24])[CH:20]=[C:19](Cl)[N:18]=1.O>CN(C=O)C>[Cl:16][C:17]1[N:22]=[C:21]([C:23]([O:25][CH3:26])=[O:24])[CH:20]=[C:19]([N:8]([CH2:7][CH:5]2[CH2:4][O:3][C:2]([CH3:13])([CH3:1])[O:6]2)[S:9]([CH3:12])(=[O:10])=[O:11])[N:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylateHCID 54158307HCID 54158307, compound

Product 1

HCID 89423187HCID 89423187, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-bc7adf33f4ba479694910e2d248892d6
Source dataset
uspto-grants-2015_10
Patent number
US09163008B2

Reaction notes

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