Triethylamine → HCID 58015762, compound

HRID 2189280Notes

Reaction equation

HRID 2189280 reaction equation
[CH2:1]([N:4]([C:10]1[C:15](Br)=[CH:14][N:13]=[C:12]([Cl:17])[N:11]=1)[CH:5]([CH2:8][CH3:9])[CH2:6][CH3:7])[CH:2]=[CH2:3].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:17][C:12]1[N:13]=[CH:14][C:15]2[C:2]([CH3:3])=[CH:1][N:4]([CH:5]([CH2:8][CH3:9])[CH2:6][CH3:7])[C:10]=2[N:11]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 58016012HCID 58016012, compound

Product 1

HCID 58015762HCID 58015762, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of allyl-(5-bromo-2-chloro-pyrimidin-4-yl)-(1-ethyl-propyl)-amine (2.76 g, 8.7 mmol) in anhydrous DMF (15 ml) was added 8 mol % of Pd(OAc)2 (156 mg, 0.69 mmol) and 8 mol % of PPh3 (182 mg, 0.69 mmol) and triethylamine (2.4 ml, 17.3 mmol) a The reaction is stirred at 100° C. overnight. The reaction mixture is diluted with EtOAc, washed with water, dried over Na2SO4, and concentrated in vacuo. Purification with column chromatography (SiO2, 1:2 EtOAC/Hexane) gives the desired product.

Workup

  1. washwashed with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customPurification with column chromatography (SiO2, 1:2 EtOAC/Hexane)

Sources & evidence

ORD record
ord-352f115d6cbc45b2826deeebaf10ffec
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

Loading…