Ammonium Chloride → HCID 86723879, compound

HRID 576774Notes

Reaction equation

HRID 576774 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[C:19](=[O:20])[N:18]([CH2:21][CH2:22][C:23](O)=[O:24])[C:17](=[O:26])[N:16]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=4)[C:15]=3[CH3:37])=[CH:12][CH:11]=[N:10]2)=[CH:5][CH:4]=1)#[N:2].O1CCCC1.B.[Cl-].[NH4+]>O1CCCC1>[OH:24][CH2:23][CH2:22][CH2:21][N:18]1[C:19](=[O:20])[C:14]([C:13]2[N:9]([C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)[N:10]=[CH:11][CH:12]=2)=[C:15]([CH3:37])[N:16]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:35])([F:36])[F:34])[CH:28]=2)[C:17]1=[O:26]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2723981Borane;tetrahydrofuran2×HCID 86723876HCID 86723876, compound

Product 1

HCID 86723879HCID 86723879, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[5-[1-(4-cyanophenyl)-1H-pyrazol-5-yl]-4-methyl-2,6-dioxo-3-(3-trifluoromethylphenyl)-2,3-dihydropyrimidin-1(6H)-yl]propanoic acid (prepared in Example 73) (36.2 mg) in tetrahydrofuran (0.5 ml) was added under ice-cooling borane tetrahydrofuran complex (0.1 ml:1.09 M tetrahydrofuran solution), and the resulting mixture was stirred at room temperature for eighteen hours. The reaction mixture was cooled again under ice-cooling and thereto was added borane tetrahydrofuran complex (0.2 ml:1.09 M tetrahydrofuran solution) and the resulting mixture was stirred at room temperature for five hours. To the reaction mixture was added saturated aqueous ammonium chloride solution (2 ml) and the resulting mixture was extracted with ethyl acetate (20 ml×2). The organic layer was washed with water (20 ml) and saturated saline (20 ml), dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol) to afford 4-[5-[3-(3-hydroxypropyl)-6-methyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-1H-pyrazol-1-yl]benzonitrile (26.2 mg).

Workup

  1. temperatureThe reaction mixture was cooled again under ice-
  2. temperaturecooling
  3. stirringthe resulting mixture was stirred at room temperature for five hours
  4. extractionthe resulting mixture was extracted with ethyl acetate (20 ml×2)
  5. washThe organic layer was washed with water (20 ml) and saturated saline (20 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol)

Sources & evidence

ORD record
ord-6e31da3c56a047d5a8781c0ea602e482
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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