Isobutylamine → Isobutyl-(8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-7-ylmethyl)-amine

HRID 898708Notes

Reaction equation

HRID 898708 reaction equation
Br[CH2:2][C:3]1[N:8]=[CH:7][N:6]2[N:9]=[CH:10][N:11]=[C:5]2[C:4]=1[CH2:12][CH2:13][CH3:14].C([O-])([O-])=O.[K+].[K+].[CH2:21]([NH2:25])[CH:22]([CH3:24])[CH3:23]>CC#N>[CH2:21]([NH:25][CH2:2][C:3]1[N:8]=[CH:7][N:6]2[N:9]=[CH:10][N:11]=[C:5]2[C:4]=1[CH2:12][CH2:13][CH3:14])[CH:22]([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 6558IsobutylamineHCID 11430Potassium CarbonateHCID 575033117-Bromomethyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine

Product 1

HCID 58661548Isobutyl-(8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-7-ylmethyl)-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 7-bromomethyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine (16.58 mmol) in CH3CN (30 ml) is added K2CO3 (9.15 g, 66.3 mmol), isobutylamine (6.6 ml, 66.3 mmol) and the mixture is stirred at room temperature overnight. The solvent is removed in vacuo and to the residue is added water (60 ml) and EtOAc (60 ml). The layers are separated and the organic layer is washed with brine (20 ml) and dried (Na2SO4). Evaporation of the solvent provides a light yellow oil, which is used in next step without further purification.

Workup

  1. customThe solvent is removed in vacuo and to the residue
  2. additionis added water (60 ml) and EtOAc (60 ml)
  3. customThe layers are separated
  4. washthe organic layer is washed with brine (20 ml)
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the solvent
  7. customprovides a light yellow oil, which
  8. customis used in next step without further purification

Sources & evidence

ORD record
ord-d18e2a2c015e447f99bc6b735389ae70
Source dataset
uspto-grants-2008_04
Patent number
US07351826B2

Reaction notes

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