Dimethylformamide dimethyl acetal → 4-Dimethylamino-3-(2-methylsulfanyl-pyrimidin-4-yl)-but-3-en-2-one

HRID 1397164Notes

Reaction equation

HRID 1397164 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([CH2:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:5][N:4]=1.[CH3:13][N:14]([CH:16](OC)OC)[CH3:15]>>[CH3:13][N:14]([CH3:16])[CH:15]=[C:9]([C:7]1[CH:6]=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:8]=1)[C:10](=[O:12])[CH3:11]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 596066061-(2-Methylsulfanyl-pyrimidin-4-yl)-propan-2-one

Product 1

HCID 679835344-Dimethylamino-3-(2-methylsulfanyl-pyrimidin-4-yl)-but-3-en-2-oneYield 49.3%

Conditions

Temperature
80 °C

Procedure

1-(2-Methylsulfanyl-pyrimidin-4-yl)-propan-2-one (17) (1.93 g, 10.59 mmol) was taken up in DMF-DMA (20 mL, 149 mmol) and the resulting reaction was warmed to 80° C. and stirred for 2 hours. The solvent was evaporated and the crude residue partitioned between DCM and water. The organic layer was washed with brine, dried with sodium sulfate, and concentrated. The crude residue was purified by flash column chromatography with a gradient of 1-12% MeOH in DCM to give the desired product as a brown/orange oil (1.24 g, 49%). MS (ES+): m/z=238.2/239.3 (100/30) [MH+]. HPLC: tR=0.78 minute over 3 minutes. Purity: 100% [HPLC (LC/MS) at 220 nm].

Workup

  1. customthe resulting reaction
  2. customThe solvent was evaporated
  3. customthe crude residue partitioned between DCM and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customThe crude residue was purified by flash column chromatography with a gradient of 1-12% MeOH in DCM

Sources & evidence

ORD record
ord-1802262de4f6431ab0ddef78dc52e80f
Source dataset
uspto-grants-2014_12
Patent number
US08901147B2

Reaction notes

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