Ammonia → HCID 86723873, compound

HRID 576770Notes

Reaction equation

HRID 576770 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](CC=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.N.C(O[BH-](O[C:46](=[O:48])[CH3:47])OC(=O)C)(=O)C.[Na+].[CH:50]([N:53](C(C)C)CC)(C)[CH3:51].C(OC(=O)C)(=[O:61])C>O1CCCC1.O.C(O)(=O)C>[C:31]([C:30]1[CH:29]=[CH:28][C:27]([N:26]2[C:22]([C:3]3[C:4](=[O:21])[N:5]([CH2:51][CH2:50][NH:53][C:46](=[O:48])[CH3:47])[C:6](=[O:61])[N:7]([C:8]4[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:16])([F:17])[F:15])[CH:9]=4)[C:2]=3[CH3:1])=[CH:23][CH:24]=[N:25]2)=[CH:34][CH:33]=1)#[N:32]

Participants

9

Reactant 5

HCID 222AmmoniaHCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86723870HCID 86723870, compound

Product 1

HCID 86723873HCID 86723873, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 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) (18.0 mg), ammonia (0.4 ml: 0.5 N tetrahydrofuran solution) and acetic acid (4 μl) in tetrahydrofuran (1.0 ml) was added sodium triacetoxyborohydride (11.9 mg) and the resulting mixture was stirred at room temperature for two hours. To the reaction mixture were added diisopropylethyl amine (48 μl) and acetic anhydride (78 μl) and the resulting mixture was stirred at 55° C. for two hours. To the reaction mixture was added water (20 ml) and the resulting mixture was extracted with ethyl acetate (20 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 N-[2-[5-[1-(4-cyanophenyl)-1H-pyrazol-5-yl]-4-methyl-2,6-dioxo-3-(3-trifluoromethylphenyl)-2,3-dihydropyrimidin-1(6H)-yl]ethyl]acetamide (7.6 mg).

Workup

  1. stirringthe resulting mixture was stirred at 55° C. for two hours
  2. extractionthe resulting mixture was extracted with ethyl acetate (20 ml×2)
  3. washThe organic layer was washed with water (10 ml) and saturated saline (10 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol)

Sources & evidence

ORD record
ord-e5d356fa56ff41af83e8b7b3fed4ccf4
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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