Isobutylamine → 7-AMINO-2,3-DIHYDRO-8-(2-METHYLPROPYL)IMIDAZO[1,2-a]PYRIMIDIN-5(8H)-ONE

HRID 1154366Notes

Reaction equation

HRID 1154366 reaction equation
[CH2:1]([NH2:5])[CH:2]([CH3:4])[CH3:3].I.CS[C:9]1[NH:10][CH2:11][CH2:12][N:13]=1.[Na].[C:15]([CH2:17][C:18](OCC)=[O:19])#[N:16]>CCO>[NH2:16][C:15]1[N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:9]2[N:10]([CH2:11][CH2:12][N:13]=2)[C:18](=[O:19])[CH:17]=1

Participants

6

Reactant 4

HCID 6558IsobutylamineHCID 7764Ethyl cyanoacetateHCID 5360545SodiumHCID 122212281H-Imidazole, 4,5-dihydro-2-(methylthio)-, hydriodide (1:1)

Product 1

HCID 131005547-AMINO-2,3-DIHYDRO-8-(2-METHYLPROPYL)IMIDAZO[1,2-a]PYRIMIDIN-5(8H)-ONE

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 29.25 g. (0.40 mole) isobutylamine and 48.82 g. (0.20 mole) 2-(methylthio)-2-imidazoline hydroiodide in 250 ml. abs. EtOH were refluxed for 2 hr. The mixture was concentrated in vacuo to a viscous oil, which was dissolved in 100 ml. abs. EtOH and added to a solution of 8.40 g. (0.80 mole) sodium and 22.62 g. (0.20 mole) ethyl cyanoacetate in 1200 ml. abs. EtOH. The mixture was refluxed for 3 hr., then concentrated in vacuo to a viscous oil. Water (400 ml.) was added and a white solid slowly crystallized. The solid was filtered and air-dried to yield 35.43 g. (86%), mp 235°-238° (two crops). Recrystallization from CH3CN gave white crystals, mp 230.5°-232.5° (corr.).

Workup

  1. additionA mixture of 29.25 g
  2. concentrationThe mixture was concentrated in vacuo to a viscous oil, which
  3. dissolutionwas dissolved in 100 ml
  4. additionEtOH and added to a solution of 8.40 g
  5. temperatureThe mixture was refluxed for 3 hr
  6. concentration, then concentrated in vacuo to a viscous oil
  7. additionWater (400 ml.) was added
  8. customa white solid slowly crystallized
  9. filtrationThe solid was filtered
  10. customair-dried
  11. customto yield 35.43 g
  12. customRecrystallization from CH3CN
  13. customgave white crystals, mp 230.5°-232.5° (corr.)

Sources & evidence

ORD record
ord-749a190358cd45669c9fa84c49be53d7
Source dataset
uspto-grants-1984_12
Patent number
US04489078

Reaction notes

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