Hydrochloric Acid → N-{3-[(Z)-2-(4-Aminopyridin-2-yl)vinyl]phenyl}-2,5-dichloropyrimidin-4-amine Dihydrochloride

HRID 541848Notes

Reaction equation

HRID 541848 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11](/[CH:15]=[CH:16]\[C:17]3[CH:22]=[C:21]([NH:23]C(=O)OC(C)(C)C)[CH:20]=[CH:19][N:18]=3)[CH:12]=[CH:13][CH:14]=2)[C:5]([Cl:31])=[CH:4][N:3]=1.[ClH:32]>O1CCOCC1>[ClH:1].[ClH:32].[NH2:23][C:21]1[CH:20]=[CH:19][N:18]=[C:17](/[CH:16]=[CH:15]\[C:11]2[CH:10]=[C:9]([NH:8][C:6]3[C:5]([Cl:31])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)[CH:14]=[CH:13][CH:12]=2)[CH:22]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57962220tert-Butyl [2-((Z)-2-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}vinyl)pyridin-4-yl]carbamate

Product 1

HCID 86636271N-{3-[(Z)-2-(4-Aminopyridin-2-yl)vinyl]phenyl}-2,5-dichloropyrimidin-4-amine DihydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a mixture of tert-butyl [2-((Z)-2-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}vinyl)pyridin-4-yl]carbamate (73.6 mg, 0.16 mmol) in 1,4-dioxane (0.50 mL) was added 4 M of hydrogen chloride in 1,4-dioxane (0.70 mL). The resultant reaction mixture was stirred at rt for 1 hour. The reaction mixture was concentrated under vacuum to give the desired product as a light yellow powder (66 mg, 95%). LCMS for C17H14Cl2N5 (M+H)+: m/z=358.0.

Workup

  1. customThe resultant reaction mixture
  2. concentrationThe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-4119829dc0984d88a0dbe7b294449381
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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