Acetic Acid → HCID 86723872, compound

HRID 576769Notes

Reaction equation

HRID 576769 reaction equation
[CH3:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[CH2:6][N:5]([CH2:18][CH:19]=O)[C:4](=[O:21])[C:3]=1[C:22]1[N:26]([C:27]2[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=2)[N:25]=[CH:24][CH:23]=1.[CH3:35][NH:36][CH3:37].C(O)(=[O:40])C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.O>[CH3:35][N:36]([CH3:37])[CH2:19][CH2:18][N:5]1[C:4](=[O:21])[C:3]([C:22]2[N:26]([C:27]3[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=3)[N:25]=[CH:24][CH:23]=2)=[C:2]([CH3:1])[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:16])([F:15])[F:17])[CH:9]=2)[C:6]1=[O:40]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86723870HCID 86723870, compound

Product 1

HCID 86723872HCID 86723872, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[5-[6-methyl-4-oxo-3-(2-oxoethyl)-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-1H-pyrazol-1-yl]benzonitrile (prepared in Example 68) (12.8 mg), dimethyl amine (133 μl) and acetic acid (10 μl) in tetrahydrofuran (1.0 ml) was added sodium triacetoxyborohydride (8.5 mg) and the resulting mixture was stirred at room temperature for four hours. To the reaction mixture was added water (10 ml) and the resulting mixture was extracted with ethyl acetate (10 ml×2). The organic layer was washed with water (10 ml) and saturated saline (10 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-(2-dimethylaminoethyl)-6-methyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-1H-pyrazol-1-yl]benzonitrile (7.4 mg).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (10 ml×2)
  2. washThe organic layer was washed with water (10 ml) and saturated saline (10 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-f6f2fb188a6646f2adf4b679e8ffe5a0
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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