Hydrochloric Acid → HCID 66893833, compound

HRID 2357265Notes

Reaction equation

HRID 2357265 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 crystallized 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 crystallized from i-PrOH/H2O (1:1)

Sources & evidence

ORD record
ord-b35f3960d09a466f8636e3b7acca4bf6
Source dataset
uspto-grants-2010_07
Patent number
US07759486B2

Reaction notes

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