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

HRID 541872Notes

Reaction equation

HRID 541872 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:18]=[C:19]([NH:23]C(=O)OC(C)(C)C)[CH:20]=[N:21][CH:22]=3)[CH:12]=[CH:13][CH:14]=2)[C:5]([F:31])=[CH:4][N:3]=1.CO.[ClH:34]>O1CCOCC1>[ClH:1].[ClH:34].[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]([F:31])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)[CH:14]=[CH:13][CH:12]=2)[CH:22]=[N:21][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 57962649tert-Butyl [5-(2-{3-[(2-chloro-5-fluoropyrimidin-4-yl)amino]phenyl}ethyl)pyridin-3-yl]carbamate

Product 1

HCID 86636276N-{3-[2-(5-Aminopyridin-3-yl)ethyl]phenyl}-2-chloro-5-fluoropyrimidin-4-amine DihydrochlorideYield 97%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Into a reaction flask were added tert-butyl [5-(2-{3-[(2-chloro-5-fluoropyrimidin-4-yl)amino]phenyl}ethyl)pyridin-3-yl]carbamate (48 mg, 0.11 mmol), methanol (0.50 mL) and 4.0 M of hydrogen chloride in 1,4-dioxane (0.50 mL). The reaction mixture was stirred at rt for 2 h and then concentrated under vacuum to give the desired product as an off-white powder (35 mg, 97%). LCMS for C17H16ClFN5 (M+H)+: m/z=344.0.

Workup

  1. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2da32ddd56e94e7c88db1ce971d6447d
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

Loading…