Sodium Carbonate → Bmy 21502

HRID 1761390Notes

Reaction equation

HRID 1761390 reaction equation
O.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH2:5][CH2:4]1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:23]1[CH:28]=[CH:27][N:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[N:24]=1>CO>[F:30][C:29]([F:32])([F:31])[C:25]1[N:26]=[C:27]([N:3]2[CH2:4][CH2:5][CH:6]([CH2:9][N:10]3[CH2:14][CH2:13][CH2:12][C:11]3=[O:15])[CH2:7][CH2:8]2)[CH:28]=[CH:23][N:24]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 152943694-Chloro-2-(trifluoromethyl)pyrimidineHCID 20081755HCID 20081755, compound

Product 1

HCID 129930Bmy 21502Yield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the procedure described above in Examples 2 and 3, a mixture of 1-[(4-piperidinyl)methyl]-2-pyrrolidinone hydrochloride (II, 21.85 g, 0.1 mole) and sodium carbonate (26.5 g, 0.25 mole) in methanol (150 mL) was refluxed for one hour. The methanol was then removed in vacuo, and acetonitrile (150 mL) was added to the residue. The mixture was cooled and stirred as 4-chloro-2-(trifluoromethyl)pyrimidine (18.28 g, 0.2 mole) was added. The mixture was stirred at room temperature for 18 hours and then filtered and the filtrate concentrated in vacuo to give a thick residue which solidified upon being washed with hexane (100 mL). The light tan powder (23.8 g, 73%) which resulted was chromatographed (5% methanol/ethyl acetate on silica) to give 19.8 g as white crystals, m.p. 118.5°-120.5°.

Workup

  1. temperaturewas refluxed for one hour
  2. customThe methanol was then removed in vacuo, and acetonitrile (150 mL)
  3. additionwas added to the residue
  4. temperatureThe mixture was cooled
  5. additionwas added
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo
  8. customto give a thick residue which
  9. washupon being washed with hexane (100 mL)

Sources & evidence

ORD record
ord-6a101a175bee4479a5ea48103927ea25
Source dataset
uspto-grants-1989_05
Patent number
US04826843

Reaction notes

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