Isopropylamine → N-isopropyl-6-methyl-2-(methylthio)pyrimidin-4-amine

HRID 886793Notes

Reaction equation

HRID 886793 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].Cl[C:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[C:8]([S:13][CH3:14])[N:7]=1>C1COCC1>[CH:1]([NH:4][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[C:8]([S:13][CH3:14])[N:7]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 2411634-Chloro-6-methyl-2-(methylthio)pyrimidine

Product 1

HCID 55250529N-isopropyl-6-methyl-2-(methylthio)pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Isopropylamine (100 mL) was added very slowly to 22.0 g (125.96 mmol) of crude 4-chloro-6-methyl-2-(methylthio)pyrimidine in 70 mL of THF in a 350 mL pressure tube. NOTE: Residual POCl3 caused smoking and bubbling, therefore the addition was done at 0° C. Once acid was quenched, an additional 50 mL of isopropylamine was added and the pressure tube was sealed. The reaction vessel was brought to 60° C. and stirred overnight. The LCMS indicate very little starting material. Solvent was evaporated leaving N-isopropyl-6-methyl-2-(methylthio)pyrimidin-4-amine as a viscous yellow oil. The crude material was taken directly to the next step.

Workup

  1. customResidual POCl3 caused smoking and bubbling
  2. additionthe addition
  3. customwas done at 0° C
  4. customOnce acid was quenched
  5. additionan additional 50 mL of isopropylamine was added
  6. customthe pressure tube was sealed
  7. customwas brought to 60° C.
  8. customSolvent was evaporated

Sources & evidence

ORD record
ord-c6eb644b5fde45dabe033df837da9ab6
Source dataset
uspto-grants-2012_08
Patent number
US08247408B2

Reaction notes

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