Triethylamine → HCID 86617584, compound

HRID 2234425Notes

Reaction equation

HRID 2234425 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH:10]1([NH:15][CH2:16][CH2:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13][CH2:12][CH2:11]1.C(N(CC)CC)C>C(#N)C>[Br:1][C:2]1[C:3]([N:15]([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[CH2:16][CH2:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 62326761HCID 62326761, compound2×

Product 1

HCID 86617584HCID 86617584, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

5-Bromo-2,4-dichloropyrimidine (Aldrich; 1.825 g, 8.00 mmol), 3-(cyclopentylamino)-N-ethyl-propanamide (Intermediate 141; 1.48 g, 8.00 mmol) and triethylamine (1.2 mL, 8.16 mmol) were combined in acetonitrile (50 mL) and heated at 100° C. for 4 hours. The solvent was removed under reduced pressure and the residue taken up in Ethyl Acetate, washed with water and purified by flash silica chromatography (companion, 40 g, 0-10% Methanol/DCM) to give the title compound as a brown oil, (2.14 g, 71%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. washwashed with water
  3. custompurified by flash silica chromatography (companion, 40 g, 0-10% Methanol/DCM)

Sources & evidence

ORD record
ord-43bb23c3dc394b29bfeb4c19cd32cb36
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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