Diisopropylethylamine → HCID 66977024, compound

HRID 712161Notes

Reaction equation

HRID 712161 reaction equation
Cl.[CH3:2][C:3]1([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.[Br:23][C:24]1[CH:25]=[N:26][C:27](Cl)=[N:28][CH:29]=1>CCO>[Br:23][C:24]1[CH:25]=[N:26][C:27]([N:6]2[CH2:7][CH2:8][C:3]([CH3:2])([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:5]2)=[N:28][CH:29]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 19361804Ethyl 4-methylpiperidine-4-carboxylate hydrochloride

Product 1

HCID 66977024HCID 66977024, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of ethyl 4-methylpiperidine-4-carboxylate hydrochloride (0.9 g, 4.35 mmol) in EtOH (10 mL) was added DIPEA (2.30 mL, 13 mmol) at rt. The resulted mixture was stirred at rt for 10 minutes followed by addition of 5-bromo-2-chloropyrimidine (0.7 g, 3.6 mmol). The mixture was heated up to 70° C. for 1 h. After completion of reaction (by TLC), solvent was evaporated and the crude residue was purified over 100-200 M silica-gel by using 1.5% EtOAc:hexane to obtain the desired product as an off white solid compound (0.90 g, 75%). 1H NMR (DMSO-d6): δ 1.17 (s, 3H), 1.21 (t, J=7.20 Hz, 3H) 1.40 (m, 2H), 2.00 (m, 2H), 3.24 (m, 2H), 4.11 (m, 2H), 4.15 (q, J=7.20 Hz, 2H), 8.43 (s, 2H). MS: 328.08 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-88a4300bc1514fb7bf23dfd4d24596db
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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