2-Aminopyrimidine → 2-(4-Hydroxy-3-methoxyphenyl)imidazo[1,2-a]pyrimidine

HRID 340657

Reaction equation

HRID 340657 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9]Br)=[CH:4][C:3]=1[O:12][CH3:13].[NH2:14][C:15]1[N:20]=[CH:19][CH:18]=[CH:17][N:16]=1>C(#N)C>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:14]=[C:15]3[N:20]=[CH:19][CH:18]=[CH:17][N:16]3[CH:9]=2)=[CH:4][C:3]=1[O:12][CH3:13]

Participants

4

Reactant 2

HCID 79782-AminopyrimidineHCID 135422582-Bromo-1-(4-hydroxy-3-methoxyphenyl)ethan-1-one

Product 1

HCID 698104562-(4-Hydroxy-3-methoxyphenyl)imidazo[1,2-a]pyrimidineYield 62.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

To 30 ml of an acetonitrile solution of 3.9 g (16 mmol) of 4′-hydroxy-3′-methoxy-2-bromoacetophenone was added 3.2 g (34 mmol) of 2-aminopyrimidine, and the mixture was stirred at 65° C. for 2 hours. The precipitated crystals were suction filtered and dissolved in 100 ml of 50% methanol. This solution was mixed with 1.3 g of sodium hydrogencarbonate and stirred at room temperature for 10 minutes. The precipitated crystals were suction filtered, and recrystallized from 50 ml of 50% methanol, thereby giving 2.4 g of 2-(4-hydroxy-3-methoxyphenyl)imidazo[1,2-a]pyrimidine in an yield of 62%.

Workup

  1. filtrationfiltered
  2. dissolutiondissolved in 100 ml of 50% methanol
  3. additionThis solution was mixed with 1.3 g of sodium hydrogencarbonate
  4. stirringstirred at room temperature for 10 minutes
  5. filtrationfiltered
  6. customrecrystallized from 50 ml of 50% methanol

Sources & evidence

ORD record
ord-59315116c28b4b959b943af348105111
Source dataset
uspto-grants-2014_11
Patent number
US08895599B2

Linked notes

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