Hexane → HCID 23144188, compound

HRID 337470Notes

Reaction equation

HRID 337470 reaction equation
CC1(C)CCCC(C)(C)N1.C([Li])CCC.CCCCCC.[O:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:27]1[N:28]=[C:29]([NH:38][C:39]([C:41]2[CH:46]=[CH:45][N:44]=[CH:43][CH:42]=2)=[O:40])[S:30][C:31]=1[C:32](=[O:37])N(OC)C.[N:47]1[CH:52]=[CH:51][CH:50]=[N:49][CH:48]=1.[Cl-].[NH4+]>C1COCC1>[O:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:27]1[N:28]=[C:29]([NH:38][C:39]([C:41]2[CH:42]=[CH:43][N:44]=[CH:45][CH:46]=2)=[O:40])[S:30][C:31]=1[C:32]([C:52]1[CH:51]=[CH:50][N:49]=[CH:48][N:47]=1)=[O:37]

Participants

8

Reactant 6

HCID 8058HexaneHCID 9260PyrimidineHCID 130352,2,6,6-TetramethylpiperidineHCID 25517Ammonium ChlorideHCID 23144082HCID 23144082, compoundHCID 178418339Butyllithium

Product 1

HCID 23144188HCID 23144188, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2,2,6,6-Tetramethylpiperidine (0.233 mL, 1.38 mmol) was dissolved in THF (6 mL), and a 1.58 mol/L solution of n-butyllithium in n-hexane (0.880 mL, 1.38 mmol) was added thereto in a stream of argon at −78° C., followed by stirring at room temperature for 30 minutes. At −78° C., a solution of Compound 98 (150 mg, 0.419 mmol) and pyrimidine (0.0990 mL, 1.26 mmol) in THF (2 mL) was added to the reaction mixture, followed by stirring at room temperature for 2 hours. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (ethyl acetate) to afford the entitled Compound 375 (11.0 mg, 7%).

Workup

  1. customat −78° C.
  2. stirringby stirring at room temperature for 2 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled away under reduced pressure
  7. customThe resulting residue was purified through silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-6ad9598ae854473db5cfb12b16649f14
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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