Hydrochloric Acid → HCID 118093137, compound

HRID 2207402Notes

Reaction equation

HRID 2207402 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:4]=[C:5]([C:20]2[CH:21]=[CH:22][C:23]([C:26]#[N:27])=[N:24][CH:25]=2)[CH:6]=[C:7]([NH:9][C:10]2[N:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][N:11]=2)[CH:8]=1>[Pd].C(O)C>[ClH:1].[NH2:27][CH2:26][C:23]1[N:24]=[CH:25][C:20]([C:5]2[CH:6]=[C:7]([NH:9][C:10]3[N:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][N:11]=3)[CH:8]=[C:3]([CH3:2])[CH:4]=2)=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131735908HCID 131735908, compound

Product 1

HCID 118093137HCID 118093137, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

HCl (4 M in dioxanes, 0.844 mL, 3.38 mmol) followed by palladium on carbon (599 mg, 0.281 mmol) were added to a mixture of 5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridine-2-carbonitrile (1.00 g, 2.81 mmol) and ethanol (200 mL). The reaction mixture was purged and flushed with H2(g) and was stirred under 1 atm of H2(g) for 3.5 hours at room temperature. The reaction mixture was filtered through CELITE, washed with ethanol and ethyl acetate and concentrated under reduced pressure to afford N-{3-[6-(Aminomethyl)pyridin-3-yl]-5-methylphenyl}-4-(trifluoromethyl)pyrimidin-2-amine hydrochloride as a yellow powder. MS APCI calc'd for C18H17F3N5 [M+H]+ 360. found 360.

Workup

  1. customThe reaction mixture was purged
  2. customflushed with H2(g)
  3. filtrationThe reaction mixture was filtered through CELITE
  4. washwashed with ethanol and ethyl acetate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d790a40ed36e43c294f37dfa770f18ad
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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