Methyl iodide → HCID 20626960, compound

HRID 270721Notes

Reaction equation

HRID 270721 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:30]=[CH:29][CH:28]=[CH:27][C:5]=1[O:6][C:7]1[C:24](=[O:25])[N:23]([CH3:26])[C:10]2[N:11]=[C:12]([NH:15][CH:16]3[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18][CH2:17]3)[N:13]=[CH:14][C:9]=2[CH:8]=1.[CH3:31]I>O1CCCC1.[Ag]=O.[N+]([O-])([O-])=O.[Ag+]>[F:3][C:4]1[CH:30]=[CH:29][CH:28]=[CH:27][C:5]=1[O:6][C:7]1[C:24](=[O:25])[N:23]([CH3:26])[C:10]2[N:11]=[C:12]([NH:15][CH:16]3[CH2:21][CH2:20][CH:19]([O:22][CH3:31])[CH2:18][CH2:17]3)[N:13]=[CH:14][C:9]=2[CH:8]=1

Participants

7

Reactant 3

HCID 6328Methyl iodide2×HCID 14798Sodium HydroxideHCID 20626959HCID 20626959, compound

Product 1

HCID 20626960HCID 20626960, compound

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 92152Silver(II) oxideCatalyst2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a slurry of freshly prepared silver oxide (filtered/dried from an aqueous mixture of silver nitrate, 0.44 g, 2.70 mmol) and sodium hydroxide (0.21 g, 5.20 mmol)) in 2 mL tetrahydrofuran was added pyrimidin-7(8H)-one (Step A, 0.20 g, 0.52 mmol) and methyl iodide (0.065 mL, 1.04 mmol). After stirring at 50° C. for three days, additional silver oxide and methyl iodide (0.98 mL, 15.7 mmol) were added; the temperature was increased to reflux and the reaction continued for 2 weeks. Following this time period, the mixture was cooled to room temperature, evaporated and purified by column chromatography (SiO2, CH2Cl2/MeOH/NH4OH—90/9/1). Fractions containing product were combined and evaporated under reduced pressure to provide the free amine. This was dissolved in methanol (1-2 mL) and hydrochloric acid in ether (1M, 1.0 eq) was added. Isolation of the solid via filtration, rinsing with ether and drying provided 0.030 g of the hydrochloride salt (Mass spec. M+1=399, MP=135.0-145.0° C.).

Workup

  1. temperaturethe temperature was increased
  2. temperatureto reflux
  3. waitthe reaction continued for 2 weeks
  4. temperaturethe mixture was cooled to room temperature
  5. customevaporated
  6. custompurified by column chromatography (SiO2, CH2Cl2/MeOH/NH4OH—90/9/1)
  7. additionFractions containing product
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8a4a38b4f07c4887b07bd0941fc321d8
Source dataset
uspto-grants-2008_11
Patent number
US07449581B2

Reaction notes

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