1-Methyl-3-triphenylmethyl-5-methoxycarbonyl-1,4,5,6-tetrahydropyrimidinium iodide → 1-Methyl-5-methoxycarbonyl-1,4,5,6-tetrahydropyrimidine

HRID 1653731Notes

Reaction equation

HRID 1653731 reaction equation
[I-].[CH3:2][NH+:3]1[CH2:8][CH:7]([C:9]([O:11][CH3:12])=[O:10])[CH2:6][N:5](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:4]1>C(O)(C(F)(F)F)=O>[CH3:2][N:3]1[CH2:8][CH:7]([C:9]([O:11][CH3:12])=[O:10])[CH2:6][N:5]=[CH:4]1

Participants

3

Reactant 1

HCID 867464331-Methyl-3-triphenylmethyl-5-methoxycarbonyl-1,4,5,6-tetrahydropyrimidinium iodide

Product 1

HCID 152943851-Methyl-5-methoxycarbonyl-1,4,5,6-tetrahydropyrimidine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Procedure

1-Methyl-3-triphenylmethyl-5-methoxycarbonyl-1,4,5,6-tetrahydropyrimidinium iodide (395 mg, 0.75 mmol) is dissolved in TFA (1 ml) with stirring in a stoppered round bottom flask at room temperature. After 18 hours stirring the excess TFA is evaporated in vacuo, and the dark residue triturated with ether. The ether is decanted leaving an oily residue that is taken up in ice cold sat. Na2CO3 and then extracted with chloroform. After drying and evaporation the chloroform fraction gave the free base which is recrystallized (chloroform/hexane) to yellow crystals 88 mg (74%) identified by 300 MHz nmr, ms m/z=156.

Workup

  1. customis evaporated in vacuo
  2. customthe dark residue triturated with ether
  3. customThe ether is decanted
  4. customleaving an oily residue that
  5. extractionextracted with chloroform
  6. customAfter drying
  7. customevaporation the chloroform fraction
  8. customgave the free base which
  9. customis recrystallized (chloroform/hexane) to yellow crystals 88 mg (74%)

Sources & evidence

ORD record
ord-ec064ac194d745708f7edfd8ccb79054
Source dataset
uspto-grants-1995_04
Patent number
US05403845

Reaction notes

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