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

HRID 541840Notes

Reaction equation

HRID 541840 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]=[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]([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]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57961542tert-Butyl [2-(2-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}ethyl)pyridin-4-yl]carbamate

Product 1

HCID 86636269N-{3-[2-(4-Aminopyridin-2-yl)ethyl]phenyl}-2,5-dichloropyrimidin-4-amine DihydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a mixture of tert-butyl [2-(2-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}ethyl)pyridin-4-yl]carbamate (0.75 g, 1.6 mmol) in 1,4-dioxane (3.0 mL) was added 4 M hydrogen chloride in 1,4-dioxane (7.1 mL). The resultant reaction mixture was stirred at rt for 2 hours. The reaction mixture was concentrated under vacuum to give the desired product as a light yellow powder (0.67 g, 95%). LCMS for C17H16Cl2N5 (M+H)+: m/z=360.2, 362.0.

Workup

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

Sources & evidence

ORD record
ord-0c5baf139136401088d29a93512aa4c3
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

Loading…