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

HRID 1775311Notes

Reaction equation

HRID 1775311 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[NH2:10][C:11]1([CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:15][CH2:14][CH2:13][CH2:12]1.BrC1C(NCCNC(=O)OC(C)(C)C)=NC(Cl)=NC=1>>[Br:1][C:2]1[C:3]([NH:10][C:11]2([CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:12][CH2:13][CH2:14][CH2:15]2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 2899735-Bromo-2,4-dichloropyrimidineHCID 52908198tert-butyl N-((1-aminocyclopentyl)methyl)carbamateHCID 86695590tert-butyl N-[2-[(5-bromo-2-chloro-pyrimidin-4-yl)amino]ethyl]carbamate

Product 1

HCID 86695607tert-butyl N-[[1-[(5-bromo-2-chloro-pyrimidin-4-yl)amino]cyclopentyl]methyl]carbamate

Procedure

tert-butyl N-[[1-[(5-bromo-2-chloro-pyrimidin-4-yl)amino]cyclopentyl]methyl]carbamate is synthesized by treating 5-Bromo-2,4-dichloropyrimidine with tert-butyl N-[(1-aminocyclopentyl)methyl]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-5ee3716f19e84f5e90bab8fe6ff2a6f6
Source dataset
uspto-grants-2016_02
Patent number
US09260442B2

Reaction notes

Loading…