Triethylamine → HCID 58015762, compound

HRID 2189296Notes

Reaction equation

HRID 2189296 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, compoundYield 45.9%

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) is added Pd(OAc)2 (156 mg, 0.69 mmol) and PPh3 (182 mg, 0.69 mmol) and triethylamine (2.4 mL, 17.3 mmol). The reaction mixture 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, EtOAC/hexane 1:2) gives 0.95 g of 2-chloro-7-(1-ethyl-propyl)-5-methyl-7H-pyrrolo[2,3-d]pyrimidine.

Workup

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

Sources & evidence

ORD record
ord-a8ef28bc62ef4495b79d34341f82a94d
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

Loading…