2-Chloro-4,6-dimethylpyrimidine → (1R,6S)-8-(4,6-Dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane

HRID 1193059Notes

Reaction equation

HRID 1193059 reaction equation
[CH:1]12[N:8]([C:9]3C=N[C:16]4[C:11](=[CH:12]C=[CH:14][CH:15]=4)[N:10]=3)[CH2:7][CH:6]1[CH2:5][CH2:4][NH:3][CH2:2]2.C(OC([N:26]1CCC2C(NC2)C1)=O)(C)(C)C.ClC1N=C(C)C=C(C)N=1.ClC1C=NC2C(=CC=CC=2)N=1>>[CH3:14][C:15]1[CH:16]=[C:11]([CH3:12])[N:10]=[C:9]([N:8]2[C@@H:1]3[C@@H:6]([CH2:5][CH2:4][NH:3][CH2:2]3)[CH2:7]2)[N:26]=1

Participants

5

Reactant 4

HCID 205502-Chloro-4,6-dimethylpyrimidineHCID 2389382-ChloroquinoxalineHCID 43810891Tert-butyl 3,8-diazabicyclo[4.2.0]octane-3-carboxylateHCID 671166512-(3,8-Diaza-bicyclo[4.2.0]oct-8-yl)-quinoxaline

Product 1

HCID 68156939(1R,6S)-8-(4,6-Dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane

Procedure

The title compound was prepared in a manner analogous to Intermediate 2, substituting (1S,6R)3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester for 3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester and 2-chloro-4,6-dimethyl-pyrimidine for 2-chloro-quinoxaline in Step A. MS (ESI) mass calcd. for C12H18N4, 218.3; m/z found, 219.2 [M+H]+. 1H NMR (CDCl3): 6.31 (s, 1H), 4.25-4.16 (m, 1H), 4.02 (t, J=7.6, 1H), 3.71 (dd, J=8.0, 3.1, 1H), 3.59 (dd, J=14.5, 1.5, 1H), 3.14-3.05 (m, 1H), 2.94 (dd, J=14.5, 3.8, 1H), 2.67-2.56 (m, 2H), 2.28 (s, 6H), 2.11-1.98 (m, 2H), 1.76-1.62 (m, 1H).

Sources & evidence

ORD record
ord-d92fa7442c0948f6a329e2c629eac71e
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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