Methyl iodide → HCID 178503546, compound

HRID 1094491Notes

Reaction equation

HRID 1094491 reaction equation
[O:1]=[C:2]1[NH:7][C:6](=[S:8])[NH:5][C:4]([CH2:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([C:20]([OH:22])=[O:21])=[CH:15][CH:14]=[CH:13]3)=[CH:3]1.[OH-].[Na+].[CH3:25]I>C1COCC1.O>[OH:1][C:2]1[N:7]=[C:6]([S:8][CH3:25])[N:5]=[C:4]([CH2:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([C:20]([OH:22])=[O:21])=[CH:15][CH:14]=[CH:13]3)[CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 86665166HCID 86665166, compound

Product 1

HCID 178503546HCID 178503546, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.30 g (7.37 mMol) 6-(6-oxo-2-thioxo-1,2,3,6-tetrahydro-pyrimidin-4-ylmethyl)-naphthalene-1-carboxylic acid are suspended in 160 ml THF. Then a solution of 452 mg (11.3 mMol) NaOH in 9 ml water is added, followed by 556 μl (8.93 mMol) methyliodide. After 15 h, the reaction mixture is concentrated in vacuo. The residue is used without further purification in Step 3.8. Pure title compound can be obtained by chromatography (Combi Flash; CH2Cl2→CH2Cl2/MeOH 7:1): TLC (CH2Cl2/MeOH 4:1): Rf=0.46.

Workup

  1. concentrationthe reaction mixture is concentrated in vacuo
  2. customThe residue is used without further purification in Step 3.8

Sources & evidence

ORD record
ord-c835a81748c94977b13618ea2369af57
Source dataset
uspto-grants-2012_03
Patent number
US08133886B2

Reaction notes

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