Hydrochloric Acid → N-{4-Amino-3-[2-(5-aminopyridin-3-yl)ethyl]benzyl}-2,5-dichloropyrimidin-4-amine trihydrochloride

HRID 1614984Notes

Reaction equation

HRID 1614984 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]2[C:22]([Cl:23])=[CH:21][N:20]=[C:19]([Cl:24])[N:18]=2)=[CH:11][C:10]=1[CH2:25][CH2:26][C:27]1[CH:28]=[C:29]([NH:33]C(=O)OC(C)(C)C)[CH:30]=[N:31][CH:32]=1)=O)(C)(C)C.CO.[ClH:43]>O1CCOCC1>[ClH:23].[ClH:43].[ClH:23].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]2[C:22]([Cl:23])=[CH:21][N:20]=[C:19]([Cl:24])[N:18]=2)=[CH:11][C:10]=1[CH2:25][CH2:26][C:27]1[CH:32]=[N:31][CH:30]=[C:29]([NH2:33])[CH:28]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 58467874HCID 58467874, compound

Product 1

HCID 86643683N-{4-Amino-3-[2-(5-aminopyridin-3-yl)ethyl]benzyl}-2,5-dichloropyrimidin-4-amine trihydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Into a reaction flask were added tert-butyl {5-[2-(2-[(tert-butoxycarbonyl)amino]-5-{[(2,5-dichloropyrimidin-4-yl)amino]methyl}phenyl)ethyl]pyridin-3-yl}carbamate (0.44 g, 0.75 mmol), methanol (3 mL), and a solution of hydrogen chloride in 1,4-dioxane (5 mL, 4.0 M). The reaction mixture was stirred at rt overnight and concentrated under vacuum to give the desired product as a white powder (0.40 g, 98%). LCMS for C18H19Cl2N6 (M+H)+: m/z=389.0, 391.0.

Workup

  1. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ab74b4e473ee41589888264be644125d
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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