2-Chloropyrimidine → HCID 178511661, compound

HRID 1631448Notes

Reaction equation

HRID 1631448 reaction equation
[C@H:1]1([NH2:8])[CH2:6][CH2:5][C@H:4]([NH2:7])[CH2:3][CH2:2]1.Cl[C:10]1[N:15]=[CH:14][CH:13]=[CH:12][N:11]=1>O>[N:11]1[CH:12]=[CH:13][CH:14]=[N:15][C:10]=1[NH:7][C@H:4]1[CH2:5][CH2:6][C@H:1]([NH2:8])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 744042-ChloropyrimidineHCID 178511674HCID 178511674, compound

Product 1

HCID 178511661HCID 178511661, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A stirred mixture of trans-1,4-cyclohexanediamine (1.50 g, 13.1 mmol) and 2-chloropyrimidine (500 mg, 4.37 mmol) was heated at 160° C. for 2 h then cooled to RT. The mixture was diluted with water, filtered, and the aqueous phase was extracted three times with ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated to afford 22A (235 mg, 28%). MS (ES): m/z=193 [M+H]+.

Workup

  1. temperaturethen cooled to RT
  2. filtrationfiltered
  3. extractionthe aqueous phase was extracted three times with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ca7385d38e7848d88bfede58d30a3533
Source dataset
uspto-grants-2014_07
Patent number
US08791257B2

Reaction notes

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