4,6-Dichloropyrimidine → HCID 59777368, compound

HRID 1013078Notes

Reaction equation

HRID 1013078 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([NH2:11])[CH2:8][CH2:9][CH3:10])[CH:2]=1.[Cl:12][C:13]1[CH:18]=[C:17](Cl)[N:16]=[CH:15][N:14]=1.C(N(C(C)C)CC)(C)C>C(O)C>[Cl:12][C:13]1[N:14]=[CH:15][N:16]=[C:17]([NH:11][CH:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH2:8][CH2:9][CH3:10])[CH:18]=1

Participants

5

Reactant 3

HCID 709434,6-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 119721371-(3-Pyridyl)-1-butylaMine

Product 1

HCID 59777368HCID 59777368, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-pyridin-3-ylbutan-1-amine (100 mg, 0.67 mmol) in ethanol (4 mL) was added 4,6-dichloropyrimidine (109 mg, 0.73 mmol) and diisopropylethylamine (232 μL, 1.33 mmol). The solution was stirred for 3 days after which time the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (25 mL) and washed with H2O (3×15 mL), brine (15 mL) and dried (Na2SO4). The residue remaining after concentration in vacuo was chromatographed using ethyl acetate-hexanes (4:6-9:1) as eluant to separate the desired product (28 mg).

Workup

  1. customwas removed under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (25 mL)
  3. washwashed with H2O (3×15 mL), brine (15 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationafter concentration in vacuo
  6. customwas chromatographed
  7. customto separate the desired product (28 mg)

Sources & evidence

ORD record
ord-5b626d5139a8412796c40e4a45fbcfa9
Source dataset
uspto-grants-2011_07
Patent number
US07981900B2

Reaction notes

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