n-(2-{[4-(2,4-Dichlorophenyl)-5-(hydroxymethyl)pyrimidin-2-yl]amino}ethyl)(tert-butoxy)carboxamide → {2-[(2-Aminoethyl)amino]-4-(2,4-dichlorophenyl)pyrimidin-5-yl]methan-1-ol

HRID 1825533Notes

Reaction equation

HRID 1825533 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([CH2:15][OH:16])=[CH:13][N:12]=[C:11]([NH:17][CH2:18][CH2:19][NH:20]C(OC(C)(C)C)=O)[N:10]=1>FC(F)(F)C(O)=O>[NH2:20][CH2:19][CH2:18][NH:17][C:11]1[N:10]=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[C:14]([CH2:15][OH:16])=[CH:13][N:12]=1

Participants

3

Reactant 1

HCID 22142949n-(2-{[4-(2,4-Dichlorophenyl)-5-(hydroxymethyl)pyrimidin-2-yl]amino}ethyl)(tert-butoxy)carboxamide

Product 1

HCID 22142936{2-[(2-Aminoethyl)amino]-4-(2,4-dichlorophenyl)pyrimidin-5-yl]methan-1-ol

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

N-(2-{[4-(2,4-dichlorophenyl)-5-(hydroxymethyl)pyrimidin-2-yl]amino}ethyl)(tert-butoxy)carboxamide (372 mg, 0.90 mmol) was dissolved in 2 mL of anhdyrous trifluoroacetic acid and stirred at room temperature for 2 h. Evaporation of the solvent afforded {2-[(2-aminoethyl)amino]-4-(2,4-dichlorophenyl)pyrimidin-5-yl}methan-1-ol, as its trifluoracetate salt, in quantitative yield.

Workup

  1. customEvaporation of the solvent

Sources & evidence

ORD record
ord-687fae26b0434fefbe3582d94809c1f7
Source dataset
uspto-grants-2006_05
Patent number
US07045519B2

Reaction notes

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