2-Chloro-4,5,6-trimethylpyrimidine → (1R,6S)-8-(4,5,6-Trimethylpyrimidin-2-yl)-3,8-diazabicyclo[4.2.0]octane

HRID 1193208Notes

Reaction equation

HRID 1193208 reaction equation
CC1N=C([N:8]2[C@@H:15]3[C@@H:10]([CH2:11][CH2:12][NH:13][CH2:14]3)[CH2:9]2)C=CC=1.Cl[C:17]1[N:22]=[C:21]([CH3:23])[C:20]([CH3:24])=[C:19]([CH3:25])[N:18]=1.[C@@H]12NC[C@@H]1CCN(C(OC(C)(C)C)=O)C2>>[CH3:25][C:19]1[C:20]([CH3:24])=[C:21]([CH3:23])[N:22]=[C:17]([N:8]2[C@@H:15]3[C@@H:10]([CH2:11][CH2:12][NH:13][CH2:14]3)[CH2:9]2)[N:18]=1

Participants

4

Reactant 3

HCID 125019872-Chloro-4,5,6-trimethylpyrimidineHCID 16099092cis-3-Boc-3,8-diazabicyclo[4.2.0]octaneHCID 67116915(1R,6S)-8-(6-Methylpyridin-2-yl)-3,8-diazabicyclo[4.2.0]octane

Product 1

HCID 67116795(1R,6S)-8-(4,5,6-Trimethylpyrimidin-2-yl)-3,8-diazabicyclo[4.2.0]octane

Procedure

(1R,6S)-8-(4,5,6-Trimethylpyrimidin-2-yl)-3,8-diazabicyclo[4.2.0]octane was prepared in a manner analogous to Intermediate 40, using Intermediate 66 and Intermediate 39 as starting materials. MS (ESI) mass calcd. for C13H20N4, 232.17; m/z found, 233.1 [M+H]+.

Sources & evidence

ORD record
ord-556aedb435194865a0074f62e7bf3d93
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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