Hexane → HCID 66976956, compound

HRID 712217Notes

Reaction equation

HRID 712217 reaction equation
Cl.[CH3:2][S:3]([C:6]1([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)(=[O:5])=[O:4].CCN(C(C)C)C(C)C.[Br:26][C:27]1[CH:28]=[N:29][C:30](Cl)=[N:31][CH:32]=1.CCCCCC>CCO>[Br:26][C:27]1[CH:28]=[N:29][C:30]([N:9]2[CH2:10][CH2:11][C:6]([S:3]([CH3:2])(=[O:5])=[O:4])([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:7][CH2:8]2)=[N:31][CH:32]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 66977146HCID 66977146, compound

Product 1

HCID 66976956HCID 66976956, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-(methylsulfonyl)piperidine-4-carboxylate hydrochloride (0.20 g, 0.74 mmol) in EtOH (7.0 mL) was added DIPEA (0.03 mL, 1.86 mmol) at rt and the mixture stirred at rt for 10 min followed by addition of 5-bromo-2-chloropyrimidine (0.12 g, 0.62 mmol). The reaction was then heated up to 70° C. for 1 h. After completion (by TLC), solvent was evaporated and the crude residue purified over 100-200 M silica-gel using 15% EtOAc:hexane to obtain the desired product as a yellow solid (0.108 g, 45% yield). 1H NMR (DMSO-d6): δ 1.20 (t, J=7.20 Hz, 3H), 1.62 (m, 2H), 2.07 (m, 2H), 2.69 (m, 2H), 3.69 (s, 3H), 4.62 (q, J=7.20 Hz, 2H), 4.86 (m, 2H) and 8.46 (s, 2H).

Workup

  1. temperatureThe reaction was then heated up to 70° C. for 1 h
  2. customAfter completion (by TLC), solvent was evaporated
  3. customthe crude residue purified over 100-200 M silica-gel

Sources & evidence

ORD record
ord-30db6f5a73b9456bad1d196e2e96498a
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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