Dimethylformamide dimethyl acetal → HCID 86658939, compound

HRID 1950791Notes

Reaction equation

HRID 1950791 reaction equation
COC1C=[CH:7][C:6]([C:9]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH3:20])[N:12]=[C:11]([S:21][CH3:22])[N:10]=2)=CC=1.CO[CH:25](OC)[N:26](C)[CH3:27]>CN(C=O)C.C(Cl)Cl.O>[CH3:25][N:26]([CH3:27])/[CH:7]=[CH:6]/[C:9]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH3:20])[N:12]=[C:11]([S:21][CH3:22])[N:10]=1

Participants

6

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 46838739HCID 46838739, compound

Product 1

HCID 86658939HCID 86658939, compoundYield 94.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
130 °C

Procedure

To the solution of ethyl 4-(4-methoxyphenyl)-6-methyl-2-(methylthio)pyrimidine-5-carboxylate (0.67 g, 1.75 mmol) in 5 mL DMF was added N,N-dimethylformamide dimethyl acetal (0.32 mL, 2.50 mmol). The reaction mixture was stirred at 130° C. for 2 hours. After monitoring the reaction by TLC was cooled to room temperature, then the mixture was diluted with DCM and water. After extracted three times by DCM from the aqueous layer, the combined organic layer was dried over MgSO4. The solution was condensed under reduced pressure yielding crude mixture (467 mg). The mixture was used for the next step without further purification.

Workup

  1. customthe reaction by TLC
  2. temperaturewas cooled to room temperature
  3. extractionAfter extracted three times by DCM from the aqueous layer
  4. dry with materialthe combined organic layer was dried over MgSO4
  5. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-7e4e7f0f621a4d038690869b692ee10b
Source dataset
uspto-grants-2013_03
Patent number
US08404677B2

Reaction notes

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