Water → 2,4-Dimethoxypyrimidine-5-carboxylic acid

HRID 1925032Notes

Reaction equation

HRID 1925032 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6]([CH:11]=[O:12])=[CH:5][N:4]=1.Cl([O-])=[O:14].[Na+].O.P([O-])(O)(O)=O.[Na+].O>C(O)(C)(C)C>[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6]([C:11]([OH:14])=[O:12])=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 5977822,4-Dimethoxypyrimidine-5-carbaldehydeHCID 23668197Sodium Chlorite2×

Product 1

HCID 138615652,4-Dimethoxypyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

To a solution of 2,4-Bis(methyloxy)-5-pyrimidinecarbaldehyde (commercially available from Toronto, 1.400 g, 8.33 mmol) at 0° C. in t-Butanol (14.00 mL) an aqueous solution (7 mL) of Sodium chlorite (1.807 g, 19.98 mmol) was added over 25 min and sodium dihydrogen phosphate hydrate (3.64 g, 23.33 mmol). The yellow mixture obtained was warmed to 25° C. and after 6 h 14 mL of t-Butanol, 7 mL of water, and Sodium chlorite (2.26 g, 25 mmol) were added. The reaction mixture was stirred at room temperature overnight. After 24 h, the mixture was evaporated in vacuo, and the crude material purified by SPE 25 g cartridge eluting with DCM/MeOH 8:2 to recover 1 g of title compound.

Workup

  1. customThe yellow mixture obtained
  2. additionwere added
  3. waitAfter 24 h
  4. customthe mixture was evaporated in vacuo
  5. customthe crude material purified by SPE 25 g cartridge
  6. washeluting with DCM/MeOH 8:2
  7. customto recover 1 g of title compound

Sources & evidence

ORD record
ord-3ad974546e3b4adc805b99967415a5f0
Source dataset
uspto-grants-2012_05
Patent number
US08178549B2

Reaction notes

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