Tetrahydrofuran → HCID 58890982, compound

HRID 1686977Notes

Reaction equation

HRID 1686977 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.[CH2:10]([NH2:13])[C:11]#[CH:12].C(=O)([O-])[O-].[K+].[K+].C1COCC1>O>[Cl:1][C:2]1[N:7]=[C:6]([NH:13][CH2:10][C:11]#[CH:12])[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 239041Propargylamine

Product 1

HCID 58890982HCID 58890982, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,4,5-Trichloropyrimidine (500 mg, 2.7 mmol), propargyl amine (149 mg, 2.7 mmol), and potassium carbonate (373 mg, 2.7 mmol) were combined in a 30 ml reaction vial with 5 ml THF and stirred at room temperature overnight. The reaction was poured into 50 ml water and extracted with EtOAc (3×20 ml). The combined organic was dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield (2,5-dichloro-pyrimidin-4-yl)-prop-2-ynyl-amine (488 mg, 90%) as a yellow oil that crystallizes upon standing. This was used crude in the next reaction.

Workup

  1. extractionextracted with EtOAc (3×20 ml)
  2. dry with materialThe combined organic was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4c96ee87c3de4377876c7ca08bb3dfdc
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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