Water → (E)-methyl 2-[2-(6-methylthiopyrimidin-4-yloxy)phenyl]-3-methoxypropenoate

HRID 1166152Notes

Reaction equation

HRID 1166152 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2/[C:15](=[CH:20]\[O:21][CH3:22])/[C:16]([O:18][CH3:19])=[O:17])[CH:3]=1.[CH3:23][S-:24].[Na+].O.CCOCC>C(Cl)(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCC>[CH3:23][S:24][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2/[C:15](=[CH:20]\[O:21][CH3:22])/[C:16]([O:18][CH3:19])=[O:17])[CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 4378561Sodium methanethiolateHCID 11782200Methyl (2E)-2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyprop-2-enoate

Product 1

HCID 15044821(E)-methyl 2-[2-(6-methylthiopyrimidin-4-yloxy)phenyl]-3-methoxypropenoateYield 89%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6212ChloroformSolventHCID 8058HexaneSolvent

Procedure

(E)-Methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (1.0 g), was treated with sodium methanethiolate (1.09 g) at room temperature in chloroform (15 ml) and water (10 ml) in the presence of a catalytic amount of tetrabutylammonium bromide. After stirring overnight, the chloroform layer was separated and the remaining aqueous layer was further extracted with chloroform. The combined chloroform layers were washed with water, dried and concentrated to give an orange oil. Chromatography using a mixture of ether and hexane (2:1) gave (E)-methyl 2-[2-(6-methylthiopyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (0.92 g, 89% yield) as a pale yellow oil; 1H NMR: δ 2.52(3H,s), 3.59(3H,s), 3.73(3H,s), 6.55(1H,s), 7.17(1H,d), 7.20-7.55(3H,m), 7.45(1H,s), 8.57(1H,s) ppm.

Workup

  1. customthe chloroform layer was separated
  2. extractionthe remaining aqueous layer was further extracted with chloroform
  3. washThe combined chloroform layers were washed with water
  4. customdried
  5. concentrationconcentrated
  6. customto give an orange oil

Sources & evidence

ORD record
ord-34a669bdfa384e9190306556de4f41f8
Source dataset
uspto-grants-2003_09
Patent number
US06613773B2

Reaction notes

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