Hydrochloric Acid → [(1R,3S,4S)-1-(2-Aza-bicyclo[2.2.1]hept-3-yl)methyl]-(5-bromo-pyrimidin-2-yl)-amine

HRID 882801Notes

Reaction equation

HRID 882801 reaction equation
Cl.C(OC([N:9]1[C@H:14]([CH2:15][NH:16][C:17]2[N:22]=[CH:21][C:20]([Br:23])=[CH:19][N:18]=2)[C@@H:13]2[CH2:24][C@H:10]1[CH2:11][CH2:12]2)=O)(C)(C)C>O1CCOCC1>[C@H:10]12[CH2:24][C@H:13]([CH2:12][CH2:11]1)[C@@H:14]([CH2:15][NH:16][C:17]1[N:22]=[CH:21][C:20]([Br:23])=[CH:19][N:18]=1)[NH:9]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66867454(1R,3S,4S)-3-[(5-Bromo-pyrimidin-2-ylamino)-methyl]-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Product 1

HCID 66867981[(1R,3S,4S)-1-(2-Aza-bicyclo[2.2.1]hept-3-yl)methyl]-(5-bromo-pyrimidin-2-yl)-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of HCl in dioxane (4.0 M, 30 mL) is added to a solution of (1R,3S,4S)-3-[(5-bromo-pyrimidin-2-ylamino)-methyl]-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (6.63 mmol) in dioxane (30 mL). After 4 h the solvents are removed in vacuo to give a crude product which is used without further purification. LC-MS: tR=0.64 min; [M+H]+=283.0.

Workup

  1. customAfter 4 h the solvents are removed in vacuo

Sources & evidence

ORD record
ord-2969bf3ea26b4829893f408a042bc9b9
Source dataset
uspto-grants-2012_08
Patent number
US08236801B2

Reaction notes

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