4-Chloro-6-ethylpyrimidine → HCID 51356700, compound

HRID 2401233Notes

Reaction equation

HRID 2401233 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][NH2:13])=[CH:7][CH:6]=2.Cl[C:17]1[CH:22]=[C:21]([CH2:23][CH3:24])[N:20]=[CH:19][N:18]=1>CN1CCCC1=O.C(OCC)(=O)C>[CH2:23]([C:21]1[N:20]=[CH:19][N:18]=[C:17]([NH:13][CH2:12][C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[NH:4][C:3]([C:2]([F:1])([F:14])[F:15])=[CH:11]3)[CH:22]=1)[CH3:24]

Participants

5

Reactant 2

HCID 111372714-Chloro-6-ethylpyrimidine2×HCID 58126817(2-(Trifluoromethyl)-1h-indol-5-yl)methanamine2×

Product 1

HCID 51356700HCID 51356700, compoundYield 34.7%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of {[2-(trifluoromethyl)-1H-indol-5-yl]methyl}amine (Intermediate 34, 171 mg, 0.8 mmol), 4-chloro-6-ethylpyrimidine (Intermediate 12, 171 mg, 1.200 mmol) and DI PEA (0.279 mL, 1.600 mmol) in N-methyl-2-pyrrolidone (1 mL) was heated at 100° C. for 2 hours. After cooling to room temperature the reaction mixture was diluted with ethyl acetate. The solution was washed with water and brine, dried and evaporated. The residue was purified by silica gel chromatography eluting with 50-100% ethyl acetate in isohexane to give the crude product which was triturated with ether/isohexane and the resulting colourless solid was collected, washed with cold ether and dried to give the title compound (89 mg).

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. washThe solution was washed with water and brine
  3. customdried
  4. customevaporated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 50-100% ethyl acetate in isohexane
  7. customto give the crude product which
  8. customwas triturated with ether/isohexane
  9. customthe resulting colourless solid was collected
  10. washwashed with cold ether
  11. customdried

Sources & evidence

ORD record
ord-1cf92da7355d4061b144d05a9b3e3f68
Source dataset
uspto-grants-2014_08
Patent number
US08796283B2

Reaction notes

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