N-methyl-2-pyrrolidone → HCID 68312323, compound

HRID 1472916Notes

Reaction equation

HRID 1472916 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([F:9])=[CH:4][N:3]=1.Cl.[F:11][C:12]1([F:18])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.CN1C(=O)CCC1>CCOC(C)=O>[F:11][C:12]1([F:18])[CH2:17][CH2:16][N:15]([C:2]2[N:7]=[C:6]([CH3:8])[C:5]([F:9])=[CH:4][N:3]=2)[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 27583514,4-Difluoropiperidine hydrochlorideHCID 207780732-Chloro-5-fluoro-4-methylpyrimidine

Product 1

HCID 68312323HCID 68312323, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A 5 mL microwave vial was charged with 2-chloro-5-fluoro-4-methylpyrimidine (JOC 2004, 69, 3943-3949) (0.19 g, 1.3 mmol), 4,4-difluoropiperidine hydrochloride (1.0 g, 6.5 mmol) and NMP (2.6 mL). The mixture was heated in a microwave oven at 120° C. for 24 hours then cooled to ambient temperature. The mixture was then diluted with EtOAc, washed with water (3×), and brine. The organic extract was concentrated and purified by chromatography (silica gel, 0-5% EtOAc/hexanes gradient) to afford the title compound. MS (ESI) m/z: 232.4 (M+H)+.

Workup

  1. temperaturethen cooled to ambient temperature
  2. washwashed with water (3×), and brine
  3. extractionThe organic extract
  4. concentrationwas concentrated
  5. custompurified by chromatography (silica gel, 0-5% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-d706012f0e324377b061e223dc06000b
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

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