Dimethyl Sulfoxide → 3-(2-Methyl-pyrimidin-5-yl)-5-oxo-pentanoic acid ethyl ester

HRID 2187372Notes

Reaction equation

HRID 2187372 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:13][C:14](=[O:27])[CH2:15][CH:16]([C:20]1[CH:21]=[N:22][C:23]([CH3:26])=[N:24][CH:25]=1)[CH2:17][CH2:18][OH:19])[CH3:12].CCN(CC)CC>C(Cl)Cl>[CH2:11]([O:13][C:14](=[O:27])[CH2:15][CH:16]([C:20]1[CH:21]=[N:22][C:23]([CH3:26])=[N:24][CH:25]=1)[CH2:17][CH:18]=[O:19])[CH3:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 235812815-Hydroxy-3-(2-methyl-pyrimidin-5-yl)-pentanoic acid ethyl ester

Product 1

HCID 235812803-(2-Methyl-pyrimidin-5-yl)-5-oxo-pentanoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of oxalyl chloride (73 μL, 0.84 mmol) in CH2Cl2 at −78° C. was added DMSO (80 μL, 1.0 mmol) dropwise. After gas evolution ceased, 2-5 (100 mg, 0.42 mmol) in CH2Cl2 was added. After 30 minutes, the cooling bath was removed and NEt3 (290 μL, 2.1 mmol) was added. After 20 minutes, the reaction mixture was diluted with CH2Cl2 and washed sat. NaHCO3 and brine, dried (MgSO4), and concentrated to give 2-6 as a yellow oil.

Workup

  1. customthe cooling bath was removed
  2. waitAfter 20 minutes
  3. washwashed sat. NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-96dcab0b107b49459542544b13436a9b
Source dataset
uspto-grants-2002_06
Patent number
US06410526B1

Reaction notes

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