Pyridine → HCID 70794788, compound

HRID 2088473Notes

Reaction equation

HRID 2088473 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C:13]([C:14](Cl)=[O:15])=[CH:12][N:11]([CH3:17])[C:10](=[O:18])[NH:9]2)=[CH:4][CH:3]=1.[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH:30]=[C:29]([CH3:31])[CH:28]=[N:27]2)=[CH:22][C:21]=1[NH2:32].C(#N)CC.N1C=CC=CC=1>O.C1(C)C=CC=CC=1>[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH:30]=[C:29]([CH3:31])[CH:28]=[N:27]2)=[CH:22][C:21]=1[NH:32][C:14]([C:13]1[C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[NH:9][C:10](=[O:18])[N:11]([CH3:17])[CH:12]=1)=[O:15]

Participants

7

Reactant 4

HCID 1049PyridineHCID 7854PropionitrileHCID 58128680HCID 58128680, compoundHCID 58128704HCID 58128704, compound

Product 1

HCID 70794788HCID 70794788, compoundYield 48.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

(S)-4-(4-Fluoro-phenyl)-1-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid chloride, (230 mg), prepared as in Example 1, was added to a solution of 163 mg of 2-methyl-5-(4-methyl-pyrazol-1-yl)-phenylamine, 10 mL propionitrile, and 0.1 mL pyridine. The resulting solution was heated at 100° for 30 minutes, then cooled to 50° and diluted with 5 mL water and 10 mL toluene. The mixture was vigorously stirred at 50° and the layers were separated. The warm toluene layer was washed with saturated sodium bicarbonate, and then concentrated under reduced pressure to a brown residue, which was triturated with 2 mL toluene and filtered. The resulting solid was recrystallized from ethanol/water to yield 175 mg of (S)-4-(4-fluoro-phenyl)-1-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid[2-methyl-5-(4-methyl-pyrazol-1-yl)-phenyl]-amide, MS (M+H)=420.

Workup

  1. temperatureThe resulting solution was heated at 100° for 30 minutes
  2. temperaturecooled to 50°
  3. customthe layers were separated
  4. washThe warm toluene layer was washed with saturated sodium bicarbonate
  5. concentrationconcentrated under reduced pressure to a brown residue, which
  6. customwas triturated with 2 mL toluene
  7. filtrationfiltered
  8. customThe resulting solid was recrystallized from ethanol/water

Sources & evidence

ORD record
ord-bb28ffed4a534993a3e35d0d47fbb405
Source dataset
uspto-grants-2013_05
Patent number
US08435990B2

Reaction notes

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