Water → HCID 21956060, compound

HRID 2246419Notes

Reaction equation

HRID 2246419 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6](Cl)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[N:3]=1.C(N(CC)CC)C.[H][H].O>CO.C(OCC)(=O)C.[Pd]>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][N:5]=[C:4]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[N:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 21956058HCID 21956058, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21956060HCID 21956060, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-amino-6-chloro-2-(4-fluorophenyl)-5-nitropyrimidine (15.3 g, 57 mmol) was dissolved in a mixture of methanol (200 mL) and ethyl acetate (100 mL), and after adding thereto 10% palladium on carbon (2.88 g) and triethylamine (12 mL), the mixture was stirred in a hydrogen stream for 18 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo to give a residue, to which was added water. The mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate, then concentrated in vacuo. The residue was purified by silica gel column chromatography (C-300, chloroform:methanol=20:1) to give the title compound as a brown solid (7.16 g, 68%).

Workup

  1. additionafter adding
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give a residue
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (C-300, chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-914858cda731418996ca829c05b9d8bd
Source dataset
uspto-grants-2010_03
Patent number
US07687514B2

Reaction notes

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