2-Chloropyrimidine → HCID 86748347, compound

HRID 1492904Notes

Reaction equation

HRID 1492904 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:15][CH2:14][NH:13][CH:12]2[CH3:16])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:18]1[N:23]=[CH:22][CH:21]=[CH:20][N:19]=1.C(N(C(C)C)CC)(C)C>C(O)CCCC>[N:19]1[CH:20]=[CH:21][CH:22]=[N:23][C:18]=1[N:13]1[CH2:14][CH2:15][C@@H:11]([C:8]2[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=2)[C@@H:12]1[CH3:16]

Participants

5

Reactant 3

HCID 744042-ChloropyrimidineHCID 81531DiisopropylethylamineHCID 15767027HCID 15767027, compound

Product 1

HCID 86748347HCID 86748347, compound

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

1.4 g (0.0065 mol) of the substituted pyrrolidine prepared in (d), 0.74 (0.0065 mol) g of chloropyrimidine and 0.83 g (0.0065 mol) of diisopropylethylamine were mixed together in 40 mL pentanol and refluxed under nitrogen for six hours. The pentanol was distilled off under reduced pressure. The residue was taken up in dichloromethane and washed three times with water. The solution was dried over MgSO4 and filtered. The solvent was evaporated off under reduced pressure. Column chromatography using a toluene/ethylacetate mixture as the eluent afforded both the cis and trans isomers stereochemically pure in a 2:1 ratio in a yield of 1.36 g (70 percent of theoretical). Elemental analysis indicated the following:

Workup

  1. temperaturerefluxed under nitrogen for six hours
  2. distillationThe pentanol was distilled off under reduced pressure
  3. washwashed three times with water
  4. dry with materialThe solution was dried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was evaporated off under reduced pressure
  7. customafforded

Sources & evidence

ORD record
ord-cbabc7daa7c242e9849a7f77cf508cb6
Source dataset
uspto-grants-1994_12
Patent number
US05376659

Reaction notes

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