Diisopropylethylamine → HCID 61688035, compound

HRID 417870Notes

Reaction equation

HRID 417870 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][C:14]#[CH:15])(=O)=O)=CC=1.[N:16]1([C:22]2[N:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(N(C(C)C)CC)(C)C>ClCCCl>[CH2:12]([N:19]1[CH2:20][CH2:21][N:16]([C:22]2[N:23]=[CH:24][CH:25]=[CH:26][N:27]=2)[CH2:17][CH2:18]1)[CH2:13][C:14]#[CH:15]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 887471-(2-Pyrimidinyl)piperazineHCID 2720203-Butynyl p-toluenesulfonate

Product 1

HCID 61688035HCID 61688035, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of but-3-ynyl 4-methylbenzenesulfonate (1.14 g), 2-(piperazin-1-yl)pyrimidine (1.06 g) and diisoproylethylamine (1.24 mL) in 1,2-dichloroethane (6 mL) was heated to reflux overnight. The mixture was concentrated, diluted with sat. aq. NaHCO3 (5 mL) and extracted with DCM (2×50 mL). Drying (Na2SO4) and silica gel flash chromatography (EtOAc/hexane 1:1→1:0) afforded 2-(4-(but-3-ynyl)piperazin-1-yl)pyrimidine (0.60 g).

Workup

  1. temperatureto reflux overnight
  2. concentrationThe mixture was concentrated
  3. additiondiluted with sat. aq. NaHCO3 (5 mL)
  4. extractionextracted with DCM (2×50 mL)
  5. dry with materialDrying (Na2SO4) and silica gel flash chromatography (EtOAc/hexane 1:1→1:0)

Sources & evidence

ORD record
ord-ed4bed43bf73479bb7a06917e6dcc1db
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

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