4-Chloro-N,N,6-trimethylpyrimidin-2-amine → (1R,6S)-[2-(3,8-Diaza-bicyclo[4.2.0]oct-8-yl)-6-methyl-pyrimidin-4-yl]-dimethyl-amine

HRID 1193060Notes

Reaction equation

HRID 1193060 reaction equation
[CH:1]12[N:8]([C:9]3C=N[C:16]4[C:11](=CC=[CH:14][CH:15]=4)[N:10]=3)[CH2:7][CH:6]1[CH2:5][CH2:4][NH:3][CH2:2]2.C(O[C:24]([N:26]1CCC2C(NC2)[CH2:27]1)=O)(C)(C)C.ClC1C=C(C)N=C(N(C)C)[N:36]=1.ClC1C=NC2C(=CC=CC=2)N=1>>[C@@H:1]12[N:8]([C:9]3[N:10]=[C:11]([N:26]([CH3:27])[CH3:24])[CH:16]=[C:15]([CH3:14])[N:36]=3)[CH2:7][C@@H:6]1[CH2:5][CH2:4][NH:3][CH2:2]2

Participants

5

Reactant 4

HCID 219604-Chloro-N,N,6-trimethylpyrimidin-2-amineHCID 2389382-ChloroquinoxalineHCID 43810891Tert-butyl 3,8-diazabicyclo[4.2.0]octane-3-carboxylate2×HCID 671166512-(3,8-Diaza-bicyclo[4.2.0]oct-8-yl)-quinoxaline

Product 1

HCID 68156890(1R,6S)-[2-(3,8-Diaza-bicyclo[4.2.0]oct-8-yl)-6-methyl-pyrimidin-4-yl]-dimethyl-amine

Procedure

The title compound was prepared in a manner analogous to Intermediate 2, substituting (1R,6S)-(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 4-chloro-2-dimethylamino-6-methylpyrimidine for 2-chloro-quinoxaline in Step A. The residue was purified (FCC, SiO2, MeOH (2M NH3)/DCM, 0-10%). MS (ESI) mass calcd. for C13H21N5, 247.34; m/z found 248.1 [M+H]+. 1H NMR (CDCl3): 5.40 (s, 1H), 4.21-4.10 (m, 1H), 3.85 (t, J=7.4, 1H), 3.63-3.49 (m, 2H), 3.33 (s, 1H), 3.09 (d, J=9.3, 7H), 2.97 (dd, J=14.3, 3.8, 1H), 2.71-2.52 (m, 2H), 2.19 (s, 3H), 2.09-1.97 (m, 1H), 1.77-1.59 (m, 1H).

Workup

  1. customThe residue was purified (FCC, SiO2, MeOH (2M NH3)/DCM, 0-10%)

Sources & evidence

ORD record
ord-09f2b933890b4a6b9c4846be07d82d28
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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