Methyl iodide → HCID 20626960, compound

HRID 1375582Notes

Reaction equation

HRID 1375582 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-6df13074b826449d8c791b7d050d5c6f
Source dataset
uspto-grants-2007_01
Patent number
US07169794B2

Reaction notes

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