Ethyl Acetate → 5-Bromo-2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methyl-N-(pyrrolidin-1-yl)pyrimidin-4-amine

HRID 641683Notes

Reaction equation

HRID 641683 reaction equation
[Br:1][C:2]1[C:3]([NH:16][NH2:17])=[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].[CH3:18][C:19](N(C)C)=O.[CH3:24][CH2:25]OC(C)=O>>[Br:1][C:2]1[C:3]([NH:16][N:17]2[CH2:18][CH2:19][CH2:25][CH2:24]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]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 31374DimethylacetamideHCID 592589011-(5-Bromo-2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methylpyrimidin-4-yl)hydrazine

Product 1

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

Conditions

Temperature
60 °C

Procedure

To a flask was added 1-(5-bromo-2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methylpyrimidin-4-yl)hydrazine (100 mg, 0.34 mmol) 1,4-dibromobutane (0.04 ml, 0.37 mmol) hunig's base (0.18 ml, 1.01 mmol) and DMAC (1.0 ml) at R.T. After heating at 60° C. over night, the reaction mixture was cooled to R.T. and diluted with EtOAc (2 ml) the white solid was filtered and the mother liquor was concentrated under reduced pressure. The resulting residue was purified by column chromatography eluted with 30% EtOAc:hex to give the titled compound weighted 76 mg 64%

Workup

  1. temperaturethe reaction mixture was cooled to R.T.
  2. filtrationwas filtered
  3. concentrationthe mother liquor was concentrated under reduced pressure
  4. customThe resulting residue was purified by column chromatography
  5. washeluted with 30% EtOAc

Sources & evidence

ORD record
ord-07381ae7b8e64c82b3eb2c104e3f2d70
Source dataset
uspto-grants-2010_04
Patent number
US07696213B2

Reaction notes

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