Dimethylformamide dimethyl acetal → HCID 86658932, compound

HRID 1950777Notes

Reaction equation

HRID 1950777 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:16]([CH3:23])[N:15]=[C:14]([S:24][CH3:25])[N:13]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.CO[CH:28](OC)[N:29]([CH3:31])[CH3:30]>CN(C=O)C.C(Cl)Cl.O>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([NH:11][C:12]2[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:16](/[CH:23]=[CH:28]/[N:29]([CH3:31])[CH3:30])[N:15]=[C:14]([S:24][CH3:25])[N:13]=2)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

6

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 66984909HCID 66984909, compound

Product 1

HCID 86658932HCID 86658932, compoundYield 102%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
130 °C

Procedure

To the solution of ethyl 4-(3,5-dimethoxyphenylamino)-6-methyl-2(methylthio)pyrimidine-5-carboxylate (2.7 g, 7.4 mmol) in 30 mL DMF was added N,N-dimethylformamide dimethylacetal (1.58 mL, 11.1 mmol). The reaction mixture was stirred at 130° C. for 2 hour. 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 (3.16 g). 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-827148eb60c549d1b78e96cf0765cc2e
Source dataset
uspto-grants-2013_03
Patent number
US08404677B2

Reaction notes

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