Hydrochloric Acid → HCID 66893833, compound

HRID 556591Notes

Reaction equation

HRID 556591 reaction equation
C1COCC1.[CH2:6]([O:8][C:9](=[O:37])/[CH:10]=[CH:11]/[C:12]1[C:13]([NH:28][C:29]2[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:30]=2[F:36])=[N:14][C:15]([S:26][CH3:27])=[N:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[CH3:25])C.Cl.CCOC(C)=O>CO.O>[CH3:6][O:8][C:9](=[O:37])[CH2:10][CH2:11][C:12]1[C:13]([NH:28][C:29]2[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:30]=2[F:36])=[N:14][C:15]([S:26][CH3:27])=[N:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[CH3:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 10276274(E)-3-[4-(2,6-difluoro-phenylamino)-6-(4-fluoro-2-methyl-phenyl)-2-methylsulfanyl-pyrimidin-5-yl]-acrylic acid ethyl ester

Product 1

HCID 66893833HCID 66893833, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of SmI2 in THF (0.1M) (Aldrich) (15 mL, 1 5 mmol) and MeOH (3 mL) was added the product of Example 30 (100 mg, 0.22 mmol) and the reaction mixture maintained its blue color. The presence of new product and the disappearance of starting material was indicated by hplc. After 30 min, the reaction was diluted with H2O (10 mL), then 1 M HCl (3 mL), followed by EtOAc (20 mL), the layers were shaken together and separated. The aq phase was washed with EtOAc (20 mL) and the combined EtOAc was dried (MgSO4) and the solvent was evaporated in vacuo and the residue was crystalized from i-PrOH/H2O (1:1) to afford 3-[4-(2,6-difluoro-phenylamino)-6-(4-fluoro-2-methyl-phenyl)-2-methylsulfanyl-pyrimidin-5-yl]-propionic acid methyl ester. LC MS (m/e)=448.2 (MH+), Rt=2.17 min.

Workup

  1. temperaturethe reaction mixture maintained its blue color
  2. customseparated
  3. washThe aq phase was washed with EtOAc (20 mL)
  4. dry with materialthe combined EtOAc was dried (MgSO4)
  5. customthe solvent was evaporated in vacuo
  6. customthe residue was crystalized from i-PrOH/H2O (1:1)

Sources & evidence

ORD record
ord-1f919c8d578e4b4f878f4f2b6bdb8c71
Source dataset
uspto-grants-2011_11
Patent number
US08058282B2

Reaction notes

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