Potassium Carbonate → HCID 58280180, compound

HRID 2189123Notes

Reaction equation

HRID 2189123 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3[C:22]([O:24][C@@H:25]4[CH2:30][CH2:29][CH2:28][NH:27][CH2:26]4)=[N:21][CH:20]=[N:19][C:18]=3[O:17][C:16]=2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])=[CH:11][CH:10]=1)[CH3:8].[CH3:38][O:39][C:40](=[O:45])[CH2:41][CH2:42][CH2:43]Br>C1COCC1.C(#N)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:38][O:39][C:40](=[O:45])[CH2:41][CH2:42][CH2:43][N:27]1[CH2:28][CH2:29][CH2:30][C@@H:25]([O:24][C:22]2[C:23]3[C:15]([C:12]4[CH:13]=[CH:14][C:9]([CH2:7][CH3:8])=[CH:10][CH:11]=4)=[C:16]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[F:37])[O:17][C:18]=3[N:19]=[CH:20][N:21]=2)[CH2:26]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 107604Methyl 4-bromobutyrateHCID 58280099HCID 58280099, compound

Product 1

HCID 58280180HCID 58280180, compound

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Add 1677 mg (12.1 mmol) of potassium carbonate to a solution of 2250 mg (4.9 mmol) of 5-(4-ethylphenyl)-6-(2-fluorophenyl)-4-[(3R)-piperidin-3-yloxy]furo[2,3-d]pyrimidine in 100 ml of THF and 10 ml of acetonitrile. Then add 0.74 ml (1054 mg, 5.8 mmol) of 4-brombutyric acid methyl ester and 72 mg (0.19 mmol) of tetra-n-butylammonium iodide. Stir the reaction mixture at 80° C. for 13 hours. After cooling to room temperature, filter off the residue, wash with THF, concentrate the filtrate under reduced pressure and purify the residue by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:2). 2005 mg (75% of theory) of the target compound are obtained.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationfilter off the residue
  3. washwash with THF
  4. concentrationconcentrate the filtrate under reduced pressure
  5. custompurify the residue by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:2)
  6. custom2005 mg (75% of theory) of the target compound are obtained

Sources & evidence

ORD record
ord-62fcffdb2f0a488798884b5eca0a30db
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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