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Hydrochloric Acid → HCID 66893833, compound

HRID 2249783
Notes
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Reaction equation

HRID 2249783 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 887
Methanol
Solvent
HCID 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-476b06248c9449b29d95c05f1f82acf6
Source dataset
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07314881B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes