Isoamylamine → (6-Chloro-5-propyl-pyrimidin-4-ylmethyl)-(3-methyl-butyl)-amine

HRID 898703Notes

Reaction equation

HRID 898703 reaction equation
Br[CH2:2][C:3]1[C:8]([CH2:9][CH2:10][CH3:11])=[C:7]([Cl:12])[N:6]=[CH:5][N:4]=1.[CH2:13]([NH2:18])[CH2:14][CH:15]([CH3:17])[CH3:16].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:12][C:7]1[N:6]=[CH:5][N:4]=[C:3]([CH2:2][NH:18][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:8]=1[CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 7894IsoamylamineHCID 11430Potassium CarbonateHCID 223131604-Bromomethyl-5-propyl-6-chloro-pyrimidine

Product 1

HCID 58661552(6-Chloro-5-propyl-pyrimidin-4-ylmethyl)-(3-methyl-butyl)-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 4-bromomethyl-5-propyl-6-chloro-pyrimidine (10 mmol) and isoamylamine (4.35 g, 50 mmol) in acetonitrile (30 mL) is added excess K2CO3 (6.9 g). The mixture is stirred at room temperature overnight. The solvent is removed in vacuo and water (10mL) and DCM (15 mL) are added. The layers are separated and the aqueous layer is extracted with DCM (2×15 mL). The combined extracts are washed with brine (10 ML) and dried (Na2SO4) and solvent evaporated to provide the title product as an oil.

Workup

  1. customThe solvent is removed in vacuo and water (10mL) and DCM (15 mL)
  2. additionare added
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with DCM (2×15 mL)
  5. washThe combined extracts are washed with brine (10 ML)
  6. dry with materialdried (Na2SO4) and solvent
  7. customevaporated

Sources & evidence

ORD record
ord-c541b5ce50f645b09ad378d972436e62
Source dataset
uspto-grants-2008_04
Patent number
US07351826B2

Reaction notes

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