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

HRID 541853Notes

Reaction equation

HRID 541853 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23]C(=O)OC(C)(C)C)[CH: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:19]1[CH:18]=[C:17]([CH2:16][CH2:15][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]=[CH:21][N:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57962500tert-Butyl [4-(2-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}ethyl)pyridin-2-yl]carbamate

Product 1

HCID 86636272N-{3-[2-(2-Aminopyridin-4-yl)ethyl]phenyl}-2,5-dichloropyrimidin-4-amine DihydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a mixture of tert-butyl [4-(2-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}ethyl)pyridin-2-yl]carbamate (128 mg, 0.28 mmol) in 1,4-dioxane (0.64 mL) was added 4 M of hydrogen chloride in 1,4-dioxane (3.0 mL). The resultant reaction mixture was stirred at rt for 2 hours. The reaction mixture was concentrated under vacuum to give the desired product (120 mg, 100%) as a very hygroscopic off-white powder. LCMS for C17H16Cl2N5 (M+H)+: m/z=360.0

Workup

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

Sources & evidence

ORD record
ord-42dba6208c86444e8ad76c997914784f
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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