Methyl iodide → HCID 57973790, compound

HRID 1863938Notes

Reaction equation

HRID 1863938 reaction equation
[CH3:1][C:2]1[N:10]=[C:9]2[N:4]([C:5](=[S:11])[NH:6][CH2:7][CH2:8]2)[N:3]=1.I[CH3:13]>[OH-].[Na+]>[CH3:1][C:2]1[N:10]=[C:9]2[N:4]([C:5]([S:11][CH3:13])=[N:6][CH2:7][CH2:8]2)[N:3]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86224690HCID 86224690, compound

Product 1

HCID 57973790HCID 57973790, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 505 mg (3 mmol) of 2-methyl-7,8-dihydro[1,2,4]triazolo[1,5-c]pyrimidine-5(6H)-thione in 12 mL of 50% sodium hydroxide (aqueous) was treated with 0.187 mL (426 mg, 3.3 mmol) of iodomethane. The mixture was stirred vigorously at room temperature in a stoppered flask. After 2 h, the mixture was partitioned between 25 mL of dichloromethane and 12 mL of water (CAUTION: exotherm upon addition of water). The organic phase was separated, and the aqueous phase was re-extracted with an additional 5 mL of dichloromethane. The combined organic fractions were dried over magnesium sulfate, filtered, and concentrated to dryness. The residue was flash chromatographed on silica gel (99:1 dichloromethane:methanol) to yield the title compound as white crystals, mp 75.5-76.5° C. LC-MS 183 (M+1).

Workup

  1. customthe mixture was partitioned between 25 mL of dichloromethane and 12 mL of water (CAUTION: exotherm upon addition of water)
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was re-extracted with an additional 5 mL of dichloromethane
  4. dry with materialThe combined organic fractions were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customchromatographed on silica gel (99:1 dichloromethane:methanol)

Sources & evidence

ORD record
ord-678ccd8efa4b41498214f50ebc578cec
Source dataset
uspto-grants-2009_12
Patent number
US07625888B2

Reaction notes

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