Methanol → 2-Chloro-4-(1-ethoxyvinyl)-6-(methoxymethyl)pyrimidine

HRID 59115Notes

Reaction equation

HRID 59115 reaction equation
[CH3:1]O.[OH-].[Na+].CS([O:9][CH2:10][C:11]1[CH:16]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[CH2:18])[N:14]=[C:13]([Cl:22])[N:12]=1)(=O)=O>C1C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:22][C:13]1[N:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[CH2:18])[CH:16]=[C:11]([CH2:10][O:9][CH3:1])[N:12]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 117821115(2-Chloro-6-(1-ethoxyvinyl)pyrimidin-4-yl)methyl methanesulfonate

Product 1

HCID 1178209822-Chloro-4-(1-ethoxyvinyl)-6-(methoxymethyl)pyrimidineYield 19%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 241BenzeneSolvent

Procedure

Methanol (1.06 g, 33.1 mmol) and sodium hydroxide (5 M (aq), 2.0 mL, 9.94 mmol) were added to a solution of (2-chloro-6-(1-ethoxyvinyl)pyrimidin-4-yl)methyl methanesulfonate (1.94 g, 6.63 mmol) in benzene (25 mL). Tetrabutylammonium hydrogen sulfate (0.225 g, 0.66 mmol) was added. The mixture was stirred vigorously at rt for 6 h. The phases were separated and the organic phase was filtered through a short silica plug which was washed with 10% MeOH in EtOAc (75 mL) and the solvent was evaporated. The residue was purified by preparative HPLC to give the title compound 0.287 g (19%).

Workup

  1. customThe phases were separated
  2. filtrationthe organic phase was filtered through a short silica plug which
  3. washwas washed with 10% MeOH in EtOAc (75 mL)
  4. customthe solvent was evaporated
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-f5fe9900b09348b7b3d5513387aa17a9
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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