Cyclohexylamine → HCID 25527153, compound

HRID 390107Notes

Reaction equation

HRID 390107 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:9]1[N:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[N:10]=1.C(N(C(C)C)CC)(C)C>C(OCC)(=O)C>[Cl:16][C:11]1[CH:12]=[C:13]([Cl:15])[N:14]=[C:9]([NH:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:10]=1

Participants

5

Reactant 3

HCID 7965Cyclohexylamine2×HCID 773782,4,6-TrichloropyrimidineHCID 81531Diisopropylethylamine2×

Product 1

HCID 25527153HCID 25527153, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of cyclohexanamine (1.1 mL, 9.57 mmol) in ethyl acetate (10 mL) was added 2,4,6-trichloropyrimidine (1.0 mL, 8.70 mmol) dropwise at 0° C. followed by dropwise addition of diisopropylethylamine (1.8 mL, 10.4 mmol). The reaction was warmed to ambient temperature and stirred for 3 h. Additional cyclohexanamine (0.3 mL) and diisopropylethylamine (0.5 mL) were added. After 4 h, the mixture was diluted with ethyl acetate and washed with 20% brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The resulting oil was purified by flash chromatography on silica gel eluting with a gradient of 92:8 to 85:15 hexane/ethyl acetate to give 0.740 g (35%) of the title compound.

Workup

  1. waitAfter 4 h
  2. washwashed with 20% brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting oil was purified by flash chromatography on silica gel eluting with a gradient of 92:8 to 85:15 hexane/ethyl acetate

Sources & evidence

ORD record
ord-24a7c6a1a5774344a927c8b9157406f0
Source dataset
uspto-grants-2013_02
Patent number
US08383624B2

Reaction notes

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