Methyl iodide → Methyl 2-(2-(1H-tetrazol-1-yl)pyrimidin-5-yl)propanoate

HRID 1502154Notes

Reaction equation

HRID 1502154 reaction equation
[H-].[Na+].[N:3]1([C:8]2[N:13]=[CH:12][C:11]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:10][N:9]=2)[CH:7]=[N:6][N:5]=[N:4]1.[CH3:19]I>CN(C=O)C.C(OCC)(=O)C>[N:3]1([C:8]2[N:9]=[CH:10][C:11]([CH:14]([CH3:19])[C:15]([O:17][CH3:18])=[O:16])=[CH:12][N:13]=2)[CH:7]=[N:6][N:5]=[N:4]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 89619075Methyl 2-(2-(1H-tetrazol-1-yl)pyrimidin-5-yl)acetate

Product 1

HCID 89618816Methyl 2-(2-(1H-tetrazol-1-yl)pyrimidin-5-yl)propanoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of sodium hydride (60% dispersion in mineral oil) (19.1 mg, 0.477 mmol) in anhydrous DMF (3.2 mL) was added solution of methyl 2-(2-(1H-tetrazol-1-yl)pyrimidin-5-yl)acetate (100 mg, 0.454 mmol) in anhydrous DMF (1.4 mL) at room temperature. Stirred for 10 min, then added methyl iodide (42.6 μl, 0.681 mmol) dropwise. Stirred at room temperature for 1 h. Reaction mixture was diluted with ethyl acetate and washed with water (3 times). Organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by MPLC, eluting with 20-100% ethyl acetate/hexanes, 26 column volumes. LC/MS: [(M+1)]+=235.2;

Workup

  1. stirringStirred at room temperature for 1 h
  2. customReaction mixture
  3. washwashed with water (3 times)
  4. washOrganic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by MPLC
  8. washeluting with 20-100% ethyl acetate/hexanes, 26 column volumes

Sources & evidence

ORD record
ord-b93b350cc2bf4c908754fb07c8ad92d0
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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