Diisopropylethylamine → HCID 67152512, compound

HRID 552310Notes

Reaction equation

HRID 552310 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]3[N:14]=[C:15]([CH3:19])[N:16]=[C:17](Cl)[C:12]=3[C:11]([CH3:20])=[C:10]2[CH3:21])=[C:4]([CH3:22])[CH:3]=1.[NH:23]1[CH2:28][CH2:27][CH:26]([CH2:29][CH2:30][C:31]#[N:32])[CH2:25][CH2:24]1.C(N(CC)C(C)C)(C)C>CCO>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]3[N:14]=[C:15]([CH3:19])[N:16]=[C:17]([N:23]4[CH2:28][CH2:27][CH:26]([CH2:29][CH2:30][C:31]#[N:32])[CH2:25][CH2:24]4)[C:12]=3[C:11]([CH3:20])=[C:10]2[CH3:21])=[C:4]([CH3:22])[CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 22281400HCID 22281400, compoundHCID 582813457-(4-Bromo-2,6-dimethylphenyl)-4-chloro-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 67152512HCID 67152512, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 7-(4-bromo-2,6-dimethyl-phenyl)-4-chloro-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidine (2.0 g), 3-(piperidin-4-yl)propionitrile (1.4 g) and N,N-diisopropylethylamine (1.4 g) in EtOH (4 mL) was heated at 100° C. in a sealed tube for 11 hours. After cooling to room temperature, the solvent was removed under reduced pressure. The residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate:CHCl3=8/2/1) to obtain 3-{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl}-propionitrile (2.0 g) as a white crystal.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate:CHCl3=8/2/1)

Sources & evidence

ORD record
ord-fb6f4f8d59ac4bbe865308624aee22f0
Source dataset
uspto-grants-2011_05
Patent number
US07951811B2

Reaction notes

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