5-Bromo-2,4-dichloropyrimidine → Carbamic acid, N-[[1-[(5-bromo-2-chloro-4-pyrimidinyl)amino]cyclohexyl]methyl]-, 1,1-dimethylethyl ester

HRID 72792Notes

Reaction equation

HRID 72792 reaction equation
Br[C:2]1[C:3](Cl)=NC(Cl)=N[CH:7]=1.[Br:10][C:11]1[C:12]([NH:18][CH:19]([CH:29]([CH3:31])C)[CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[N:13][C:14]([Cl:17])=[N:15][CH:16]=1>>[Br:10][C:11]1[C:12]([NH:18][C:19]2([CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:29][CH2:31][CH2:3][CH2:2][CH2:7]2)=[N:13][C:14]([Cl:17])=[N:15][CH:16]=1

Participants

3

Reactant 2

HCID 2899735-Bromo-2,4-dichloropyrimidineHCID 86695593tert-butyl N-[2-[(5-bromo-2-chloro-pyrimidin-4-yl)amino]-3-methyl-butyl]carbamate

Product 1

HCID 86695602Carbamic acid, N-[[1-[(5-bromo-2-chloro-4-pyrimidinyl)amino]cyclohexyl]methyl]-, 1,1-dimethylethyl ester

Procedure

tert-butyl N-[[1-[(5-bromo-2-chloro-pyrimidin-4-yl)amino]cyclohexyl]methyl]carbamate was synthesized using 5-bromo-2,4-dichloro-pyrimidine and Intermediate K using analogous reaction conditions as described for tert-butyl N-[2-[(5-bromo-2-chloro-pyrimidin-4-yl)amino]-3-methyl-butyl]carbamate. 1H NMR (600 MHz, DMSO-d6) δ ppm 1.18-1.54 (m, 17H) 2.23 (d, J=14.35 Hz, 2H) 3.36 (d, J=6.44 Hz, 2H) 5.82 (s, 1H) 6.93 (s, 1H) 8.22 (s, 1H). LCMS (ESI) 419 (M+H).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-677e63fc00e9412fba8c7ae7630da3f2
Source dataset
uspto-grants-2014_09
Patent number
US08829012B2

Reaction notes

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