Sulfuric acid magnesium salt (1:1) → 4-Amino-2-(4-hydroxybutylthio)pyrimidine

HRID 357023Notes

Reaction equation

HRID 357023 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH2:9][CH2:10][CH2:11][C:12](OCC)=[O:13])[N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Al].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.O>[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[N:3]=1

Participants

7

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 5359268AluminumHCID 189367844-Amino-2-(3-ethoxycarbonylpropylthio)pyrimidineHCID 21226445Aluminium lithium hydride

Product 1

HCID 189368114-Amino-2-(4-hydroxybutylthio)pyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6.03 g (25 mmol) of 4-amino-2-(3-ethoxycarbonylpropylthio)pyrimidine in 150 ml of tetrahydrofuran, 0.949 g (150 mmol) of lithium aluminum hydride was added at room temperature, followed by stirring at 60° C. for 2 hours. After the reaction mixture was cooled, water was added little by little to decompose the excess aluminum reagent. After anhydrous magnesium sulfate was added to the mixture, the precipitate was filtered off, after which the solvent was distilled off to yield 8.85 g (88.8%, white crystal) of the desired product.

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. filtrationthe precipitate was filtered off
  3. distillationafter which the solvent was distilled off

Sources & evidence

ORD record
ord-5d1e24aefc384d8ba4fafb17322cbc64
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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