Propargyl bromide → HCID 15250441, compound

HRID 2377278Notes

Reaction equation

HRID 2377278 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8](Br)[C:9]#[CH:10]>C(O)C>[CH2:10]([NH:1][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1)[C:9]#[CH:8]

Participants

4

Reactant 2

HCID 7842Propargyl bromideHCID 79782-Aminopyrimidine

Product 1

HCID 15250441HCID 15250441, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-aminopyrimidine (2 g, 20.67 mmol) and propargyl bromide (23 mL, 20.67 mmol) in ethanol (30 mL) was heated to reflux for about 23 hours. The formed precipitate was collected by filtration, washed with ethanol and was recrystallized from ethanol. To the vacuum dried crystals was added water (10 mL) and 10% aqueous sodium hydroxide (5 mL) and the mixture was stirred at room temperature for about 30 min. The solid was collected by filtration, washed with water and was re-crystalized from water to provide Example 642. MS (ESI): m/z 134 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for about 23 hours
  3. filtrationThe formed precipitate was collected by filtration
  4. washwashed with ethanol
  5. customwas recrystallized from ethanol
  6. customTo the vacuum dried crystals
  7. additionwas added water (10 mL) and 10% aqueous sodium hydroxide (5 mL)
  8. filtrationThe solid was collected by filtration
  9. washwashed with water
  10. customwas re-crystalized from water
  11. customto provide Example 642

Sources & evidence

ORD record
ord-1f4377324dbe4f82b1814daa2c1319a6
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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