Methyl iodide → HCID 69708318, compound

HRID 1760210Notes

Reaction equation

HRID 1760210 reaction equation
C[O-].[Na+].[NH2:4][C:5]1[N:13]=[CH:12][N:11]=[C:10]2[C:6]=1[N:7]=[C:8]([C:21]1[O:22][CH:23]=[CH:24][CH:25]=1)[N:9]2[C:14]1[CH:15]=[CH:16][C:17](=[O:20])[NH:18][CH:19]=1.[ClH:26].N[C:28]1N=C(C#CC(O)(C)C)N=C2C=1N=C(C1C=CC=C(F)C=1)N2C1C=CC(=O)NC=1.Cl.C(N)C#CC.IC>CO>[ClH:26].[NH2:4][C:5]1[N:13]=[CH:12][N:11]=[C:10]2[C:6]=1[N:7]=[C:8]([C:21]1[O:22][CH:23]=[CH:24][CH:25]=1)[N:9]2[C:14]1[CH:15]=[CH:16][C:17](=[O:20])[N:18]([CH3:28])[CH:19]=1

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 12136927HCID 12136927, compoundHCID 12599999But-2-yn-1-amine hydrochlorideHCID 22597425HCID 22597425, compound

Product 1

HCID 69708318HCID 69708318, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodiummethoxide (150 mg, 2.78 mmol) was added to a methanol (8 ml) suspension of 5-[6-amino-8-(2-furyl)-9H-9-purinyl]-1,2-dihydro-2-pyridinone (400 mg, 1.36 mmol) synthesized in the same method as in Example 1 (2), (3) and (4) and Example 2, and the mixture was stirred in a nitrogen atmosphere at room temperature. After 15 minutes, iodomethane (0.26 ml, 4.18 mmol) was added thereto and further stirred for 16.5 hours. The reaction solution was concentrated, and the residue was subjected to silica gel column chromatography (eluting solvent: hexane, hexane/ethyl acetate=40:1,20:1,10:1). The crude product was suspended in ethanol, and the solid was collected by filtration and washed with ethanol and diethyl ether, to give the title compound in free form (337 mg). The resulting free compound was dissolved in methanol-4N hydrochloric acid/ethyl acetate (0.4 ml) and concentrated. The residue was crystallized from methanol/ethyl acetate/diethyl ether, and the solid was collected by filtration and washed with diethyl ether, to give the title compound (270 mg, 58%) as a pale brown solid.

Workup

  1. stirringfurther stirred for 16.5 hours
  2. concentrationThe reaction solution was concentrated
  3. washthe residue was subjected to silica gel column chromatography (eluting solvent: hexane, hexane/ethyl acetate=40:1,20:1,10:1)
  4. filtrationthe solid was collected by filtration
  5. washwashed with ethanol and diethyl ether

Sources & evidence

ORD record
ord-d8dad7fa55f54d81bdb80baf1b03613c
Source dataset
uspto-grants-2005_01
Patent number
US06841549B1

Reaction notes

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