Sodium Hydroxide → HCID 178526345, compound

HRID 2247238Notes

Reaction equation

HRID 2247238 reaction equation
CO[CH:3](OC)[C:4]1[N:9]=[CH:8][N:7]=[C:6]([OH:10])[CH:5]=1.[OH-:13].[Na+].C([O-])(O)=O.[Na+].Cl.[NH2:21]O>OS(O)(=O)=O>[OH:10][C:6]1[N:7]=[CH:8][N:9]=[C:4]([CH:3]=[N:21][OH:13])[CH:5]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate2×HCID 178499536HCID 178499536, compound

Product 1

HCID 178526345HCID 178526345, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
67 °C

Procedure

6-Dimethoxymethyl-pyrimidin-4-ol (12.5 g, 73 mmol, prepared according to the procedure of J. Adams et al Biorg. Med. Chem. Lett. 8, 22, 1998, 3111-3116) was dissolved in 0.5% aqueous H2SO4 (100 ml) and stirred at 67° C. for about 30 min. 10% aqueous H2SO4 (5 ml) was added, and the reaction was stirred at 70° C. for 1.5 h. The mixture was cooled to 5° C. and stirred. NaOH solution was added (1 N, 33 ml) followed by saturated aqueous NaHCO3 (to adjust the pH to 7.5). Hydroxylamine hydrochloride was added carefully, portionwise (50.7 g, 730 mmol), producing a peach suspension. Saturated aqueous NaHCO3 was added to bring the total reaction volume to about 700 ml and the pH back to 7.5. The mixture was stirred overnight and filtered, rinsing with H2O and then t-BuOMe to obtain 6-hydroxy-pyrimidine-4-carbaldehyde oxime as a light tan solid. MS: 140.0 (M+1), 137.9 (M−1); Calc'd. for C5H5N3O2—139.11.

Workup

  1. stirringthe reaction was stirred at 70° C. for 1.5 h
  2. temperatureThe mixture was cooled to 5° C.
  3. stirringstirred
  4. customportionwise (50.7 g, 730 mmol), producing a peach suspension
  5. stirringThe mixture was stirred overnight
  6. filtrationfiltered
  7. washrinsing with H2O

Sources & evidence

ORD record
ord-9249e568ca2244abb468727d32ae27af
Source dataset
uspto-grants-2010_03
Patent number
US07687643B2

Reaction notes

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