m-Toluidine → HCID 178494825, compound

HRID 1244765Notes

Reaction equation

Br[C:2]1[NH:3][C:4]2[C:9]([N:10]=1)=[C:8]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)[N:7]=[C:6]([CH2:17][CH2:18][O:19][CH3:20])[N:5]=2.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[CH:23]=1>>[CH3:20][O:19][CH2:18][CH2:17][C:6]1[N:5]=[C:4]2[C:9]([N:10]=[C:2]([NH:21][C:22]3[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=3)[NH:3]2)=[C:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[N:7]=1

Participants

Reactant 2

HCID 7934m-Toluidine

HCID 178494824HCID 178494824, compound

Product 1

HCID 178494825HCID 178494825, compoundYield 81%

Conditions

Temperature: 190 °C

Procedure

A suspension of 8-bromo-2-(2-methoxy-ethyl)-6-morpholin-4-yl-9H-purine (0.42 g, 1.2 mmol) in m-toluidine (0.5 mL, 3.8 eq) in a tightly stoppered flask was heated at 190° C. for 15 minutes. Column chromatography afforded [2-(2-methoxy-ethyl)-6-morpholin-4-yl-9H-purin-8-yl]-m-tolyl-amine (0.36 g, 81%) as an off-white solid.

Sources & evidence

ORD record: ord-ab45d7bf34044a63b7dbdfcfa4e40e00
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122665B2

Reaction notes

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