2,4,6-Trimethylpyridine → Ethyl 5-benzylsulfonylamino-1-methoxymethyl-3-uracilylacetate

HRID 1251346Notes

Reaction equation

HRID 1251346 reaction equation
[NH2:1][C:2]1[C:3](=[O:18])[N:4]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5](=[O:11])[N:6]([CH2:8][O:9][CH3:10])[CH:7]=1.N1C(C)=CC(C)=CC=1C.[CH2:28]([S:35](Cl)(=[O:37])=[O:36])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCCC1.C(OCC)(=O)C>[CH2:28]([S:35]([NH:1][C:2]1[C:3](=[O:18])[N:4]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5](=[O:11])[N:6]([CH2:8][O:9][CH3:10])[CH:7]=1)(=[O:37])=[O:36])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 74740Phenylmethanesulfonyl chlorideHCID 54496358Ethyl 5-amino-1-methoxymethyluracilylacetate

Product 1

HCID 22943410Ethyl 5-benzylsulfonylamino-1-methoxymethyl-3-uracilylacetate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of ethyl 5-amino-1-methoxymethyl-uracilylacetate (8.0 g, 31 mmole) and 2,4,6-collidine (13.7 mnL, 62 mmole) in tetrahydrofuran (50 mL) is cooled in an ice bath. A solution of benzylsulfonyl chloride (5.93 g, 31 mmole) in tetrahydrofuran (50 mL) is added over a 30-minute period. After addition is complete, the solution is stirred for 1 hour at 0° C., then 3 hours at room temperature. The reaction mixture is diluted with ethyl acetate, washed with 1.0N HCl (until aqueous layer is pH 1), water, saturated sodium bicarbonate, and brine. The organic layer is dried over anhydrous magnesium sulfate, and the solvent is removed. The title compound is isolated.

Workup

  1. additionAfter addition
  2. custom3 hours
  3. customat room temperature
  4. washwashed with 1.0N HCl (until aqueous layer is pH 1), water, saturated sodium bicarbonate, and brine
  5. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  6. customthe solvent is removed

Sources & evidence

ORD record
ord-01389bc1dfdc43d7a4981f7fbebb0e9d
Source dataset
uspto-grants-2002_01
Patent number
US06342504B1

Reaction notes

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