Pyrimidine, 2,4-dichloro-5-methyl- → 2-chloro-5-methyl-N-[(1S)-1-pyridin-3-ylbutyl]pyrimidin-4-amine

HRID 1013076Notes

Reaction equation

HRID 1013076 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C@@H:7]([NH2:11])[CH2:8][CH2:9][CH3:10])[CH:2]=1.[Cl:12][C:13]1[N:18]=[C:17](Cl)[C:16]([CH3:20])=[CH:15][N:14]=1.C(N(C(C)C)CC)(C)C>C(O)C>[Cl:12][C:13]1[N:18]=[C:17]([NH:11][C@H:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH2:8][CH2:9][CH3:10])[C:16]([CH3:20])=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 74508Pyrimidine, 2,4-dichloro-5-methyl-HCID 81531DiisopropylethylamineHCID 66838311(1s)-1-(3-Pyridyl)butylamine

Product 1

HCID 597773712-chloro-5-methyl-N-[(1S)-1-pyridin-3-ylbutyl]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (1S)-1-pyridin-3-ylbutan-1-amine (600 mg, 4.0 mmol) in ethanol (20 mL) was added 2,4-dichloro-5-methylpyrimdine (717 mg, 4.4 mmol) and diisopropylethylamine (1.4 mL, 8 mmol). The solution was heated at reflux for 24 h after which time the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (30 mL) and washed with H2O (2×15 mL), brine (15 mL) and dried (Na2SO4). The residue remaining after concentration in vacuo was chromatographed using ethyl acetate-hexanes (9:1) as eluant to separate the desired product (370 mg).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 24 h after which time the solvent
  3. customwas removed under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate (30 mL)
  5. washwashed with H2O (2×15 mL), brine (15 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationafter concentration in vacuo
  8. customwas chromatographed
  9. customto separate the desired product (370 mg)

Sources & evidence

ORD record
ord-a2172b5f5a014161aa5956d496b4e3bd
Source dataset
uspto-grants-2011_07
Patent number
US07981900B2

Reaction notes

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