HCID 86650583, compound → HCID 70794723, compound

HRID 2088472Notes

Reaction equation

HRID 2088472 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][O:9][C:10]1[C:11]([Cl:35])=[CH:12][C:13]([CH3:34])=[C:14]([NH:16][C:17]([C:19]2[C@H:20]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[NH:21][C:22](=[O:26])[N:23]([CH3:25])[CH:24]=2)=[O:18])[CH:15]=1)(C)(C)C>C1COCC1.O.CC(O)=O>[Cl:35][C:11]1[C:10]([O:9][CH2:8][CH2:7][OH:6])=[CH:15][C:14]([NH:16][C:17]([C:19]2[C@H:20]([C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)[NH:21][C:22](=[O:26])[N:23]([CH3:25])[CH:24]=2)=[O:18])=[C:13]([CH3:34])[CH:12]=1

Participants

5

Reactant 1

HCID 86650583HCID 86650583, compound

Product 1

HCID 70794723HCID 70794723, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

The (S)-4-(4-Fluoro-phenyl)-1-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid{5-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-4-chloro-2-methyl-phenyl}-amide from step 1 was dissolved in a mixture of 1 ml THF, 1 mL water, and 3 ml HOAc. This solution was stirred at room temperature for 18 hours, then diluted with water and extracted with ethyl acetate. The combined ethyl acetate layers were dried over Na2SO4, filtered and the solvent removed in vacuo. The residue was chromatographed in 3% MeOH/CH2Cl2 to give 50 mg of (S)-4-(4-Fluoro-phenyl)-1-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid[4-chloro-5-(2-hydroxy-ethoxy)-2-methyl-phenyl]-amide, MS (M+H)=434.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined ethyl acetate layers were dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. customThe residue was chromatographed in 3% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-a6a6ce2fe49b41a6bc69c008ca0b1f82
Source dataset
uspto-grants-2013_05
Patent number
US08435990B2

Reaction notes

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