Triethylamine → HCID 178471805, compound

HRID 1600680Notes

Reaction equation

HRID 1600680 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([NH2:12])[CH2:8][CH2:7]1)[CH3:2].Cl[C:15]1[N:20]=[CH:19][CH:18]=[CH:17][N:16]=1.C(N(CC)CC)C>C(O)C>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([NH:12][C:15]2[N:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:11]1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 744042-ChloropyrimidineHCID 178471806HCID 178471806, compound

Product 1

HCID 178471805HCID 178471805, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of trans-(4-Amino-cyclohexyl)-acetic acid ethyl ester (Karapavicius K., Palaima A. I., Knunyants I. L., Izv. Akad. Nauk SSSR, Ser. Khim., 1980;10;2374-9) (3.46 g, 18.7 mmol), 2-chloropyrimidine (2.14 g, 18.7 mmol) and triethylamine (5.21 mL) is refluxed in ethanol (EtOH) (10 mL) for 48 hours. The reaction is cooled, and the solvents are removed under reduced pressure. The residue is partitioned between chloroform and 2N aqueous sodium carbonate solution. The organic layer is separated, dried over sodium sulfate, and the solvents are removed under reduced pressure. The residue is chromatographed over silica gel using a mixture of chloroform and methanol to give trans-[4-(pyrimidin-2-ylamino)-cyclohexyl]-acetic acid ethyl ester.

Workup

  1. temperatureThe reaction is cooled
  2. customthe solvents are removed under reduced pressure
  3. customThe residue is partitioned between chloroform and 2N aqueous sodium carbonate solution
  4. customThe organic layer is separated
  5. dry with materialdried over sodium sulfate
  6. customthe solvents are removed under reduced pressure
  7. customThe residue is chromatographed over silica gel using
  8. additiona mixture of chloroform and methanol

Sources & evidence

ORD record
ord-a7782fda6a3f4f36880e91e2ed32dbfb
Source dataset
uspto-grants-1999_11
Patent number
US05977110

Reaction notes

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