Isothiocyanatotrimethylsilane → 6-(2,6-Dimethoxypyridin-3-yl)-1-(2-hydroxyethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

HRID 77539Notes

Reaction equation

HRID 77539 reaction equation
[CH3:1][O:2][C:3]1[C:8](/[C:9](/[NH:16][CH2:17][CH2:18][OH:19])=[CH:10]/[C:11]([O:13]CC)=O)=[CH:7][CH:6]=[C:5]([O:20][CH3:21])[N:4]=1.C[Si]([N:26]=[C:27]=[S:28])(C)C>CC1OCCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[C:8]([C:9]2[N:16]([CH2:17][CH2:18][OH:19])[C:27](=[S:28])[NH:26][C:11](=[O:13])[CH:10]=2)=[CH:7][CH:6]=[C:5]([O:20][CH3:21])[N:4]=1

Participants

5

Reactant 2

HCID 75297IsothiocyanatotrimethylsilaneHCID 86684678HCID 86684678, compound

Product 1

HCID 866846796-(2,6-Dimethoxypyridin-3-yl)-1-(2-hydroxyethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-oneYield 16%

Reagents, catalysts & solvents 2

HCID 73012-MethyltetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (Z)-ethyl 3-(2,6-dimethoxypyridin-3-yl)-3-((2-hydroxyethyl)amino)acrylate (100 mg, 0.34 mmol) in 2-MeTHF (1.0 mL) was added (trimethylsilyl)isothiocyanate (0.30 mL, 2.0 mmol) and the reaction mixture was heated at 80° C. for 4 hours. The cooled reaction mixture was diluted with EtOAc and washed with a saturated aqueous sodium bicarbonate solution. The layers were separated and the organic layer was concentrated in vacuo. The residue was triturated with MeOH and the resulting solids were collected by vacuum filtration to give the title compound (16 mg, 16%) as a white solid.

Workup

  1. customThe cooled reaction mixture
  2. washwashed with a saturated aqueous sodium bicarbonate solution
  3. customThe layers were separated
  4. concentrationthe organic layer was concentrated in vacuo
  5. customThe residue was triturated with MeOH
  6. filtrationthe resulting solids were collected by vacuum filtration

Sources & evidence

ORD record
ord-e4c9a06a174e4c19a14670fc15a74486
Source dataset
uspto-grants-2014_09
Patent number
US08841314B2

Reaction notes

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