Diisopropylethylamine → HCID 86608227, compound

HRID 417873Notes

Reaction equation

HRID 417873 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C:9]#[CH:10])(=O)=O.[N:11]1([C:17]2[N:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(N(C(C)C)CC)(C)C>C1COCC1>[CH2:6]([N:14]1[CH2:15][CH2:16][N:11]([C:17]2[N:18]=[CH:19][CH:20]=[CH:21][N:22]=2)[CH2:12][CH2:13]1)[CH2:7][CH2:8][C:9]#[CH:10]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 887471-(2-Pyrimidinyl)piperazineHCID 12476209Pent-4-yn-1-yl methanesulfonate

Product 1

HCID 86608227HCID 86608227, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of pent-4-ynyl methanesulfonate (1.05 g), 2-(piperazin-1-yl)pyrimidine (1.02 g) and diisoproylethylamine (1.2 mL) in THF (5 mL) was heated to reflux overnight. The mixture was concentrated, diluted with aq. NaOH 2M (10 mL) and extracted with DCM (2×50 mL). Drying (Na2SO4) and silica gel flash chromatography (EtOAc/hexane 2:1→2:0) afforded 2-(4-(pent-4-ynyl)piperazin-1-yl)pyrimidine (0.95 g).

Workup

  1. temperatureto reflux overnight
  2. concentrationThe mixture was concentrated
  3. additiondiluted with aq. NaOH 2M (10 mL)
  4. extractionextracted with DCM (2×50 mL)
  5. dry with materialDrying (Na2SO4) and silica gel flash chromatography (EtOAc/hexane 2:1→2:0)

Sources & evidence

ORD record
ord-5c93e5b9949847d5b87ec8b8fb2ee30a
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

Loading…