Methanesulfonic Acid → Methyl (2E)-2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyprop-2-enoate

HRID 1275729Notes

Reaction equation

HRID 1275729 reaction equation
[Cl:1][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[CH:15]([CH:20](OC)[O:21][CH3:22])[C:16]([O:18][CH3:19])=[O:17])[CH:3]=1.C(OC(=O)C)(=O)C.CS(O)(=O)=O>C1(C)C=CC=CC=1>[Cl:1][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

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 7918Acetic AnhydrideHCID 110136152-(2-(6-Chloro-pyrimidin-4-yloxy)-phenyl)-3,3-dimethoxy-propionic acid methyl ester

Product 1

HCID 11782200Methyl (2E)-2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyprop-2-enoateYield 98.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropanoate (17.98 g), acetic anhydride (5.16 g) and toluene (73 ml) was stirred at 90° C. for 20 minutes. Methane sulphonic acid (0.49 g) was added to the mixture and the mixture was heated at 90° C. for 1 hour. The mixture was cooled to room temperature, washed with cold water (25 ml) and with hot (50° C.) water (2×25 ml). The organic layer was evaporated at 75° C. (initially on a rotary evaporator, then at circa 15 mm Hg) to leave (E)-methyl 2-[-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxypropenoate as a solid (16.1 g).

Workup

  1. temperaturethe mixture was heated at 90° C. for 1 hour
  2. temperatureThe mixture was cooled to room temperature
  3. washwashed with cold water (25 ml) and with hot (50° C.) water (2×25 ml)
  4. customThe organic layer was evaporated at 75° C. (
  5. custominitially on a rotary evaporator

Sources & evidence

ORD record
ord-8f9bbd4b9d7e40e4ab529df70adabb56
Source dataset
uspto-grants-2000_12
Patent number
US06162916

Reaction notes

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