Sodium Hydroxide → HCID 178442421, compound

HRID 1731723Notes

Reaction equation

HRID 1731723 reaction equation
Cl.[CH2:2]([C:8]1[CH:9]=[N:10][C:11]([OH:14])=[N:12][CH:13]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[OH-].[Na+]>O>[CH2:2]([C:8]1[CH:9]=[N:10][C:11]([OH:14])=[N:12][CH:13]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178442422HCID 178442422, compound

Product 1

HCID 178442421HCID 178442421, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

While commercially available urea (6.0 g, 0.1 mol) and α-hexyl-β-dimethylaminoacrolein (18.3 g, 0.1 mol) were mixed with ethanol (70 ml) with stirring, conc. hydrochloric acid (50 ml) was added dropwise to the resulting solution, followed by heating under reflux for 1.5 hours, allowing the reaction mixture to stand at -20° C. for 16 hours to deposit crystals, and filtering off and drying the crystals to obtain 5-hexylpyrimidin-2-ol hydrochloride (yield: 97%). This hydrochloride was dissolved in pure water (30 ml), followed by adding dropwise 2N-NaOH aqueous solution, adjusting the pH of the mixture between 6~7 to deposit pale yellow crystals, filtering off the crystals and recrystallizing from a mixed solvent of n-heptanol and methanol to obtain 5-hexylpyrimidin-2-ol (8.4 g) (yield 48%).

Workup

  1. filtrationfiltering off the crystals
  2. customrecrystallizing from a mixed solvent of n-heptanol and methanol

Sources & evidence

ORD record
ord-6d2ea87b38824fe2a07c9ee0f79a9161
Source dataset
uspto-grants-1986_11
Patent number
US04623477

Reaction notes

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