Tetrahydrofuran → HCID 86723885, compound

HRID 576779Notes

Reaction equation

HRID 576779 reaction equation
COC(=O)C[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N:11]2[C:16]([CH3:17])=[C:15]([C:18]3[N:22]([C:23]4[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=4)[N:21]=[CH:20][CH:19]=3)[C:14](=[O:31])[N:13]([CH3:32])[C:12]2=[O:33])[CH:6]=1.[OH-:35].[Na+].[O:37]1[CH2:41]CCC1>>[C:29]([C:26]1[CH:27]=[CH:28][C:23]([N:22]2[C:18]([C:15]3[C:14](=[O:31])[N:13]([CH3:32])[C:12](=[O:33])[N:11]([C:7]4[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=4)[C:41]([OH:37])=[O:35])[C:16]=3[CH3:17])=[CH:19][CH:20]=[N:21]2)=[CH:24][CH:25]=1)#[N:30]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86723886HCID 86723886, compound

Product 1

HCID 86723885HCID 86723885, compound

Procedure

To a solution of 3-[5-[1-(4-cyanophenyl)-1H-pyrazol-5-yl]-3,6-dimethyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]phenylacetic acid methyl ester (prepared in Example 32) (239.6 mg) in tetrahydrofuran (2.0 ml) was added under ice-cooling sodium hydroxide (5M aqueous solution, 108 μl) and the resulting mixture was stirred at room temperature for twenty hours. The reaction mixture was washed with dietylether (15 ml), and the aqueous layer was acidified (pH=3) with potassium hydrogen sulfate and then extracted with ethyl acetate (50 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 3-(5-(1-(4-cyanophenyl)-1H-pyrazol-5-yl)-3,6-dimethyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)benzoic acid (67.2 mg).

Workup

  1. washThe reaction mixture was washed with dietylether (15 ml)
  2. extractionextracted with ethyl acetate (50 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol)

Sources & evidence

ORD record
ord-3a9c4e5ebb074919913c89d54340ca37
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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