Hexane → HCID 66977197, compound

HRID 712229Notes

Reaction equation

HRID 712229 reaction equation
Cl.[CH3:2][S:3][C:4]1([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.CCN(C(C)C)C(C)C.[Br:24][C:25]1[CH:26]=[N:27][C:28](Cl)=[N:29][CH:30]=1.CCCCCC>CCO>[Br:24][C:25]1[CH:26]=[N:27][C:28]([N:7]2[CH2:8][CH2:9][C:4]([S:3][CH3:2])([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:5][CH2:6]2)=[N:29][CH:30]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 66977253HCID 66977253, compound

Product 1

HCID 66977197HCID 66977197, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-(methylthio)piperidine-4-carboxylate hydrochloride (0.17 g, 0.75 mmol) in EtOH (10.0 mL) was added DIPEA (0.60 mL, 3.75 mmol) at rt and the mixture stirred at rt for 10 min followed by addition of 5-bromo-2-chloropyrimidine (0.18 g, 0.90 mmol). The reaction was heated up to 70° C. for 1 h. After completion of reaction (by TLC), solvent was evaporated and the crude residue purified over 100-200 M silica-gel using 3.0% EtOAc:hexane to obtain the desired product as a white solid (0.16 g, 60% yield). 1H NMR (DMSO-d6): δ 1.18 (t, J=7.20 Hz, 3H), 1.70 (m, 2H), 2.04 (s, 3H), 2.14 (m, 2H), 3.50 (m, 2H), 4.00 (m, 2H), 4.20 (q, J=7.20 Hz, 2H), and 8.46 (s, 2H).

Workup

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

Sources & evidence

ORD record
ord-3e0a548ac1b349969646a27fb3f58fc9
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

Loading…