4-Methylpiperidine → HCID 58638538, compound

HRID 646924Notes

Reaction equation

HRID 646924 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH3:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([N:16]2[CH2:17][CH2:18][CH:13]([CH3:12])[CH2:14][CH2:15]2)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 693814-MethylpiperidineHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 58638538HCID 58638538, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of 2,4-dichloro-5-nitropyrimidine (194 mg, 1.00 mmol) in THF (10 mL) at −40° C., 4-methylpiperidine (118 μL, 1.00 mmol) was added dropwise. The resulting mixture was stirred at −40° C. for 3 h and the solvent was removed in vacuo. The resulting yellow residue was chromatographed on silica (5-20% EtOAc:hexane) to obtain the title compound (103 mg, 40%). 1H-NMR (CDCl3; 400 MHz): δ 8.69 (s, 1H), 4.24 (br m, 2H), 3.10 (m, 2H, J=12.9, 2.7 Hz), 1.82-1.71 (m, 3H), 1.36-1.25 (m, 2H), 1.01 (d, 3H, J=4.8 Hz).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe resulting yellow residue was chromatographed on silica (5-20% EtOAc:hexane)

Sources & evidence

ORD record
ord-7d69c75fb76145caaebf3e650a3165a5
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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