Sodium Acetate → HCID 136088016, compound

HRID 501424Notes

Reaction equation

HRID 501424 reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[N:9][C:10]([Cl:15])=[N:11][C:12]=2Cl)[N:7]=[C:6]1[N:16]1[CH2:21][CH2:20][CH2:19][CH:18]([N:22]([CH3:30])[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:17]1)[C:2]#[C:3][CH3:4].C([O-])(=[O:33])C.[Na+]>CS(C)=O>[CH2:1]([N:5]1[C:13]2[C:12](=[O:33])[NH:11][C:10]([Cl:15])=[N:9][C:8]=2[N:7]=[C:6]1[N:16]1[CH2:21][CH2:20][CH2:19][CH:18]([N:22]([CH3:30])[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:17]1)[C:2]#[C:3][CH3:4]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 57472748HCID 57472748, compound

Product 1

HCID 136088016HCID 136088016, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture consisting of 580 mg of t-butyl N-[1-[7-(2-butynyl)-2,6-dichloro-7H-purin-8-yl]piperidin-3-yl]-N-methylcarbamate, 315 mg of sodium acetate and 6 ml of dimethyl sulfoxide was stirred in an oil bath at 120° C. for 7 hours. The reaction solution was partitioned between ethyl acetate and water, and the organic layer was washed with water and then with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, was filtered through a small amount of silica gel. The filtrate was concentrated, and the residue was crystallized with ethyl acetate-hexane to give 420 mg of t-butyl N-[1-[7-(2-butynyl)-2-chloro-6-oxo-6,7-dihydro-1H-purin-8-yl]piperidin-3-yl]-N-methylcarbamate. A mixture consisting of an 100 mg aliquot of the compound obtained above, 0.17 ml of methyl iodide, 48 mg of anhydrous potassium carbonate and 0.5 ml of N,N-dimethylformamide was stirred at room temperature for 4 hours. The reaction solution was partitioned between ethyl acetate and water, and the organic layer was washed with water and then with saturated brine. Then, the organic layer was concentrated, and the residue was purified by silica gel column chromatography using 50% ethyl acetate/hexane to give 104 mg of the title compound.

Workup

  1. customThe reaction solution was partitioned between ethyl acetate and water
  2. washthe organic layer was washed with water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationwas filtered through a small amount of silica gel
  5. concentrationThe filtrate was concentrated
  6. customthe residue was crystallized with ethyl acetate-hexane

Sources & evidence

ORD record
ord-c807b397888a48e59345f8c12c06b382
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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