Pyrrolidine → HCID 6492141, compound

HRID 1855436Notes

Reaction equation

HRID 1855436 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1>O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]([CH3:9])[CH:5]=[C:6]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[N:7]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 794712,4-Dichloro-6-methylpyrimidine

Product 1

HCID 6492141HCID 6492141, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,4-dichloro-6-methylpyrimidine (998 mg, 6.0 mmol) in tetrahydrofurane (30 mL) was added under stirring N,N-diisopropyl ethyl amine (853 mg, 6.6 mmol) and pyrrolidine (469 mg, 6.6 mmol) and the reaction was stirred over night at 20° C. The solvent was evaporated under reduced pressure and the residue was taken up in water and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated under reduced pressure to dryness. The residue was purified by column chromatography on silica gel using heptane/ethyl acetate (9:1 to 7:3 v/v) as eluent to yield the title compound (694 mg, 58%) as white crystals. MS ISP (m/e): 198.1/200.1 (100/40) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=6.35 (s, 1H), 3.44 (m, 2H), 3.30 (m, 2H), 2.29 (s, 3H), 1.94 (m, 4H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure to dryness
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ce571b3891d848cdafe7bd2975688e49
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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