Methyl iodide → HCID 69067168, compound

HRID 1436886Notes

Reaction equation

HRID 1436886 reaction equation
[O:1]=[C:2]([NH:8][CH2:9][C:10]1[N:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].I[CH3:17].[H-].[Na+]>CN(C=O)C>[O:1]=[C:2]([N:8]([CH3:17])[CH2:9][C:10]1[N:11]=[CH:12][CH:13]=[CH:14][N:15]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69066482Ethyl 2-oxo-2-[(pyrimidin-2-yl)methylamino]acetate

Product 1

HCID 69067168HCID 69067168, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution ethyl 2-oxo-2-[(pyrimidin-2-yl)methylamino]acetate from the previous step (1.0 g, 4.8 mmol) and iodomethane (0.5 mL, 8 mmol) in DMF (15 mL) was cooled to 0° C. and NaH (0.23 g of a 60% dispersion in mineral oil, 5.7 mmol) was added. The cooling bath was removed and the mixture was stirred at ambient temperature for 18 hours. Ethanol was added to quench the reaction and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using a gradient of 80-100% EtOAc in hexanes. The solvent was removed under reduced pressure from the fractions containing product to give the title compound as an oil. 1H NMR (400 MHz, DMSO-d6) δ 8.81 (m, 2H), 7.45 (m, 1H), 4.74 (m, 2H), 4.32, 4.13 (two q, rotamers, J=7 Hz, 2H), 3.08, 3.00 (two s, rotamers, 3H), 1.30, 1.08 (two t, rotamers, 3H); ES MS M+1=224.

Workup

  1. customThe cooling bath was removed
  2. additionEthanol was added
  3. customto quench
  4. customthe reaction
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by pressurized silica gel column chromatography
  7. customThe solvent was removed under reduced pressure from the fractions
  8. additioncontaining product

Sources & evidence

ORD record
ord-c2acfbc5bdca469eb7c5b004ab577b52
Source dataset
uspto-grants-2009_11
Patent number
US07619086B2

Reaction notes

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