Triethylamine → HCID 53735900, compound

HRID 1783506Notes

Reaction equation

HRID 1783506 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1.C(N(CC)CC)C.[CH2:19]1[CH:23]2[CH2:24][CH:25]([NH2:26])[CH:21]([CH2:22]2)[CH2:20]1>ClCCl>[CH:21]12[CH2:22][CH:23]([CH2:19][CH2:20]1)[CH2:24][CH:25]2[NH:26][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 98480Exo-2-bornanamineHCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile

Product 1

HCID 53735900HCID 53735900, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 10.0 g (53.9 mmol) of 4-chloro-2-(methylthio)-5-pyrimidinecarbonitrile in 100 mL of dichloromethane is added 9.0 mL (64.6 mmol) of triethylamine followed by dropwise addition of 7.0 mL (59.3 mmol) of exo-2-aminonorbornane. The reaction mixture is stirred at 0° C. for 2 hours. The resulting precipitate of triethylamine hydrochloride is filtered. The filtrate is washed three times with saturated aqueous solution of sodium bicarbonate. The aqueous phase is back extracted twice with dichloromethane. The combined organic phase is concentrated, and the residue is purified by filtering through a short column of silica gel eluted with dichloromethane to give 8.9 g (64%) of the title compound.

Workup

  1. filtrationThe resulting precipitate of triethylamine hydrochloride is filtered
  2. washThe filtrate is washed three times with saturated aqueous solution of sodium bicarbonate
  3. extractionThe aqueous phase is back extracted twice with dichloromethane
  4. concentrationThe combined organic phase is concentrated
  5. customthe residue is purified
  6. filtrationby filtering through a short column of silica gel
  7. washeluted with dichloromethane

Sources & evidence

ORD record
ord-dea467a11b1a407496123b0c2715f76e
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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