1-methyl-1H-pyrrole-2-ethylamine → HCID 178433457, compound

HRID 2290615Notes

Reaction equation

HRID 2290615 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([OH:8])[C:5]([CH3:9])=[C:4](Cl)[N:3]=1.[NH2:11][CH2:12][CH2:13][C:14]1[N:15]([CH3:19])[CH:16]=[CH:17][CH:18]=1>COCCOC>[CH3:1][C:2]1[NH:3][C:4]([NH:11][CH2:12][CH2:13][C:14]2[N:15]([CH3:19])[CH:16]=[CH:17][CH:18]=2)=[C:5]([CH3:9])[C:6](=[O:8])[N:7]=1

Participants

4

Reactant 2

HCID 5650581-methyl-1H-pyrrole-2-ethylamineHCID 1784334526-chloro-2,5-dimethyl-1H-pyrimidin-4-one

Product 1

HCID 178433457HCID 178433457, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A stirred suspension of 2.00 g (12.9 mmol) of 2,5-dimethyl-4-hydroxy-6-chloropyrimidine and 6.5 mL (52 mmol, 4 equiv.) of 2-(2-aminoethyl)-1-methylpyrrole in 10 mL of DME was heated at 90° C. for 18 hours under a dry atmosphere. The reaction mixture was cooled to 23° C. and filtered. The isolated solids were rinsed with Et2O, H2O, and MeOH and then recrystallized from MeOH to afford 2.63 g 83% (10.7 mmol) of pure product, m.p. 246°-247° C. as a white powder.

Workup

  1. temperatureThe reaction mixture was cooled to 23° C.
  2. filtrationfiltered
  3. washThe isolated solids were rinsed with Et2O, H2O, and MeOH
  4. customrecrystallized from MeOH

Sources & evidence

ORD record
ord-2e0cb06f1a004cff9c3066599c21ac7b
Source dataset
uspto-grants-1986_10
Patent number
US04617393

Reaction notes

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