Sodium methanethiolate → HCID 59432139, compound

HRID 245299Notes

Reaction equation

HRID 245299 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10](/[CH:11]=[CH:12]/Br)=[C:9]([NH2:14])[N:8]=[C:7]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([O:22][CH3:23])[C:16]=2[F:24])[N:6]=1)=[O:4].[CH3:25][S-:26].[Na+]>CS(C)=O.O>[CH3:1][O:2][C:3]([C:5]1[C:10](/[CH:11]=[CH:12]/[S:26][CH3:25])=[C:9]([NH2:14])[N:8]=[C:7]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([O:22][CH3:23])[C:16]=2[F:24])[N:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 59432096HCID 59432096, compound

Product 1

HCID 59432139HCID 59432139, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

6-Amino-5-((E)-2-bromovinyl)-2-(4-chloro-2-fluoro-3-methoxy-phenyl)pyrimidine-4-carboxylic acid methyl ester (0.915 g, 2.196 mmol) was dissolved in DMSO (10 mL) and sodium thiomethoxide (0.169 g, 2.416 mmol) was added. After 30 min at ambient temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was diluted with petroleum ether to decrease the solubility of residual DMSO, washed with water thrice, filtered and concentrated. The product was purified by flash chromatography (hexane/ethyl acetate gradient) to provide the title compound (0.510 g, 60.5% yield) as a yellow solid: 1H NMR (CDCl3) δ 7.63 (dd, 1H), 7.19 (dd, 1H), 6.74 (d, 1H), 6.32 (d, 1H), 5.34 (br s, 2H), 3.99 (d, 3H), 3.94 (s, 3H), 2.41 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate
  2. additionThe organic phase was diluted with petroleum ether
  3. washwashed with water thrice
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by flash chromatography (hexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-94a7ac615a8e4565bd037c454db61048
Source dataset
uspto-grants-2014_02
Patent number
US08658791B2

Reaction notes

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