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

HRID 1193064Notes

Reaction equation

HRID 1193064 reaction equation
C12N(C3C=NC4C(=CC=CC=4)N=3)CC1CCNC2.C(OC([N:26]1[CH2:33][CH2:32][CH:31]2[CH:28]([NH:29][CH2:30]2)[CH2:27]1)=O)(C)(C)C.Cl[C:35]1[CH:40]=[C:39]([CH3:41])[N:38]=[C:37]([N:42]([CH3:44])[CH3:43])[N:36]=1.ClC1C=NC2C(=CC=CC=2)N=1>>[CH:28]12[N:29]([C:35]3[CH:40]=[C:39]([CH3:41])[N:38]=[C:37]([N:42]([CH3:44])[CH3:43])[N:36]=3)[CH2:30][CH:31]1[CH2:32][CH2:33][NH:26][CH2:27]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 68156861[4-(3,8-Diaza-bicyclo[4.2.0]oct-8-yl)-6-methyl-pyrimidin-2-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-6-methyl-pyrimidin-2-yl)-dimethyl-amine for 2-chloro-quinoxaline in Step A. 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), 2.97-2.52 (m, 2H), 2.19 (s, 3H), 2.09-1.97 (1H), 1.77-1.59 (m, 1H)

Sources & evidence

ORD record
ord-95ecc4e533094554942d8533f0489885
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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