Pyrimidine, 2,4-dichloro-5-methyl- → HCID 89400315, compound

HRID 573976Notes

Reaction equation

HRID 573976 reaction equation
Cl.Cl.[F:3][C:4]1[CH:5]=[CH:6][C:7]([C@@H:10]([NH2:12])[CH3:11])=[N:8][CH:9]=1.[Cl:13][C:14]1[N:19]=[C:18](Cl)[C:17]([CH3:21])=[CH:16][N:15]=1.C(N(C(C)C)CC)(C)C>C(O)CCC.C(OCC)(=O)C>[Cl:13][C:14]1[N:19]=[C:18]([NH:12][C@H:10]([C:7]2[CH:6]=[CH:5][C:4]([F:3])=[CH:9][N:8]=2)[CH3:11])[C:17]([CH3:21])=[CH:16][N:15]=1

Participants

6

Reactant 3

HCID 74508Pyrimidine, 2,4-dichloro-5-methyl-HCID 81531DiisopropylethylamineHCID 89400394(S)-1-(5-Fluoropyridin-2-yl)ethanamine dihydrochloride

Product 1

HCID 89400315HCID 89400315, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of (S)-1-(5-fluoropyridin-2-yl)ethanamine dihydrochloride (prepared as described in WO2006/123113, 560 mg, 2.63 mmol), 2,4-dichloro-5-methylpyrimidine (620 mg, 2.63 mmol) and diisopropylethylamine (1.4 mL, 7.9 mmol) in n-butanol (1 mL) was stirred and heated for 45 min at 110° C. in a microwave oven. The reaction mixture was cooled to ambient temperature and diluted with ethyl acetate. The organic solution was washed with water and brine, dried (MgSO4), filtered and the solvent evaporated under reduced pressure. The residue was purified by flash chromatography (2:1 hexanes/ethyl acetate) to give the title compound (427 mg, 61%) as a yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. washThe organic solution was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customThe residue was purified by flash chromatography (2:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-e3e958130c1c42a4b42301d50a7ba799
Source dataset
uspto-grants-2015_05
Patent number
US09034311B2

Reaction notes

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