5-Bromo-2,4-dichloropyrimidine → tert-butyl N-[1-[[(5-bromo-2-chloro-pyrimidin-4-yl)amino]methyl]cyclopentyl]carbamate

HRID 1775309Notes

Reaction equation

HRID 1775309 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[NH2:10][CH2:11][C:12]1([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:16][CH2:15][CH2:14][CH2:13]1.BrC1C(NCCNC(=O)OC(C)(C)C)=NC(Cl)=NC=1>>[Br:1][C:2]1[C:3]([NH:10][CH2:11][C:12]2([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 2899735-Bromo-2,4-dichloropyrimidineHCID 16740809tert-butyl N-[1-(aminomethyl)cyclopentyl]carbamateHCID 86695590tert-butyl N-[2-[(5-bromo-2-chloro-pyrimidin-4-yl)amino]ethyl]carbamate

Product 1

HCID 89825179tert-butyl N-[1-[[(5-bromo-2-chloro-pyrimidin-4-yl)amino]methyl]cyclopentyl]carbamate

Procedure

tert-butyl N-[1-[[(5-bromo-2-chloro-pyrimidin-4-yl)amino]methyl]cyclopentyl]carbamate was synthesized by treating 5-bromo-2,4-dichloropyrimidine with tert-butyl N-[1-(aminomethyl)cyclopentyl]carbamate using similar experimental conditions as described for the synthesis of tert-butyl N-[2-[(5-bromo-2-chloro-pyrimidin-4-yl)amino]ethyl]carbamate. LCMS (ESI) 405 (M+H).

Sources & evidence

ORD record
ord-9ed5bc99649648b9a9089a47a446509f
Source dataset
uspto-grants-2016_02
Patent number
US09260442B2

Reaction notes

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