Acryloyl chloride → N-(5-Bromo-2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methylpyrimidin-4-yl)-N-(pyrrolidin-1-yl)acrylamide

HRID 2390003Notes

Reaction equation

HRID 2390003 reaction equation
[Br:1][C:2]1[C:3]([NH:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:4][C:5]([N:9]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]2[CH3:15])=[N:6][C:7]=1[CH3:8].[C:22](Cl)(=[O:25])[CH:23]=[CH2:24]>C(Cl)Cl.CCN(C(C)C)C(C)C>[Br:1][C:2]1[C:3]([N:16]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:22](=[O:25])[CH:23]=[CH2:24])=[N:4][C:5]([N:9]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]2[CH3:15])=[N:6][C:7]=1[CH3:8]

Participants

5

Reactant 2

HCID 13140Acryloyl chlorideHCID 592589815-Bromo-2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methyl-N-(pyrrolidin-1-yl)pyrimidin-4-amine

Product 1

HCID 59258866N-(5-Bromo-2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methylpyrimidin-4-yl)-N-(pyrrolidin-1-yl)acrylamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

To a reaction solution of 5-bromo-2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methyl-N-(pyrrolidin-1-yl)pyrimidin-4-amine (3.14 g, 8.97 mmol) in anhyrous methylene chloride (120 ml) and hunig's base (4.68 ml) was added slowly a solution of acryloyl chloride (0.80 ml, 9.86 mmol) in methylene chloride (30 ml) dropwise at R.T. After stirring at R.T for 60 mins, the reaction mixture was concentrated under reduced pressure and the residue was purified by 120 g column eluted with 40% ethyl acetate:hexane to give the titled product weighted 3.5 g a white solid 97%

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by 120 g column
  3. washeluted with 40% ethyl acetate

Sources & evidence

ORD record
ord-284543df837a4b89884fe1d7456caf35
Source dataset
uspto-grants-2012_09
Patent number
US08273755B2

Reaction notes

Loading…