Sodium Hydroxide → 2-Chloro-4-((cyclopropylmethoxy)methyl)-6-(1-ethoxyvinyl)pyrimidine

HRID 59118Notes

Reaction equation

HRID 59118 reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[OH-].[Na+].CS(O[CH2:13][C:14]1[CH:19]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[CH2:21])[N:17]=[C:16]([Cl:25])[N:15]=1)(=O)=O>C1C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:25][C:16]1[N:15]=[C:14]([CH2:13][O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)[CH:19]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[CH2:21])[N:17]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 75644CyclopropanemethanolHCID 117821115(2-Chloro-6-(1-ethoxyvinyl)pyrimidin-4-yl)methyl methanesulfonate

Product 1

HCID 1178213252-Chloro-4-((cyclopropylmethoxy)methyl)-6-(1-ethoxyvinyl)pyrimidineYield 14.1%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 241BenzeneSolvent

Procedure

Cyclopropylmethanol (0.368 mL, 4.66 mmol) and sodium hydroxide (aq, 5M, 0.70 mL, 3.50 mmol) were added to a solution of (2-chloro-6-(1-ethoxyvinyl)pyrimidin-4-yl)methyl methanesulfonate (682 mg, 2.33 mmol) in benzene (8 mL). Tetrabutylammonium hydrogen sulfate was added (79 mg, 0.23 mmol). The mixture was stirred vigorously at rt over night. The organic phase was filtered through a short silica plug which was washed with 10% MeOH in EtOAc (75 mL) and the solvents were evaporated. The residue was purified by preparative HPLC to give the title compound 88 mg (14%).

Workup

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

Sources & evidence

ORD record
ord-2262037c7c6b493fa83ce54741e84509
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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