Sodium Hydroxide → HCID 117821419, compound

HRID 59088Notes

Reaction equation

HRID 59088 reaction equation
CS([O:5][CH2:6][C:7]1[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[CH2:14])[N:10]=[C:9]([Cl:18])[N:8]=1)(=O)=O.[F:19][C:20]([F:25])([F:24])[CH2:21][CH2:22]O.[OH-].[Na+]>C1C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:18][C:9]1[N:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[CH2:14])[CH:12]=[C:7]([CH2:6][O:5][CH2:22][CH2:21][C:20]([F:25])([F:24])[F:19])[N:8]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 1375123,3,3-Trifluoro-1-propanolHCID 117821115(2-Chloro-6-(1-ethoxyvinyl)pyrimidin-4-yl)methyl methanesulfonate

Product 1

HCID 117821419HCID 117821419, compoundYield 11.5%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 241BenzeneSolvent

Procedure

To a solution of (2-chloro-6-(1-ethoxyvinyl)pyrimidin-4-yl)methyl methanesulfonate (0.452 g, 1.54 mmol) in benzene (7 mL) were added 3,3,3-trifluoropropan-1-ol (0.264 g, 2.32 mmol), sodium hydroxide (5 M, 0.463 mL, 2.32 mmol) and tetrabutylammonium hydrogen sulfate (0.052 g, 0.15 mmol). The mixture was stirred vigourously over night at room temperature. The mixture was filtered through a short silica plug with magnesium sulfate on top. The filter was washed with EtOAc. The mixture was purified by preparative HPLC to give 2-chloro-4-(1-ethoxyvinyl)-6-((3,3,3-trifluoropropoxy)methyl)pyrimidine 0.055 g 11%).

Workup

  1. filtrationThe mixture was filtered through a short silica plug with magnesium sulfate on top
  2. washThe filter was washed with EtOAc
  3. customThe mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-858020decce040b0a2758796bc369d3b
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

Loading…