Diisopropylethylamine → HCID 66705962, compound

HRID 1916194Notes

Reaction equation

HRID 1916194 reaction equation
Cl[C:2]1[C:7]([C:8]#[C:9][C:10]2[CH:11]=[N:12][C:13]([NH2:16])=[CH:14][CH:15]=2)=[C:6]([CH2:17][CH3:18])[N:5]=[CH:4][N:3]=1.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].CCN(C(C)C)C(C)C>O1CCOCC1>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][N:29]([C:2]2[C:7]([C:8]#[C:9][C:10]3[CH:11]=[N:12][C:13]([NH2:16])=[CH:14][CH:15]=3)=[C:6]([CH2:17][CH3:18])[N:5]=[CH:4][N:3]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 58073044HCID 58073044, compound

Product 1

HCID 66705962HCID 66705962, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

The title compound is synthesized according to general procedure GP7 (method 2) starting from 5.0 g (19.3 mmol) 4-chloro-6-ethyl-5-(6-amino-pyridin-3-ylethynyl)-pyrimidine and 4.32 g (23.2 mmol) piperazine 1-carboxylic acid tert-butyl ester using 9.86 mL (57.9 mmoL) DIPEA in 50 mL dioxane. The reaction mixture is stirred at 80° C. over night. The solvent is removed under reduced pressure. The residue is taken up in water extracted three times with ethylacetate. The combined organic layers are dried over MgSO4 filtered off and the solvent is removed under reduced pressure. The residue is purified via NP-chromatography (DCM/MeOH 75/25 as eluent) yielding 7.2 g (92%) of the desired product, which is used without further purification for the next step.

Workup

  1. customThe title compound is synthesized
  2. customThe solvent is removed under reduced pressure
  3. extractionextracted three times with ethylacetate
  4. dry with materialThe combined organic layers are dried over MgSO4
  5. filtrationfiltered off
  6. customthe solvent is removed under reduced pressure
  7. customThe residue is purified via NP-chromatography (DCM/MeOH 75/25 as eluent)

Sources & evidence

ORD record
ord-d22a4cc02a8144e98da28b8f4d083a0d
Source dataset
uspto-grants-2013_12
Patent number
US08618111B2

Reaction notes

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