4-Methoxybenzylamine → HCID 21940661, compound

HRID 1883453Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH2:15])=[CH:12][CH:11]=1>>[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH:15][C:2]2[CH:3]=[N:4][CH:5]=[N:6][CH:7]=2)=[CH:12][CH:11]=1

Participants

Reactant 2

HCID 754524-Methoxybenzylamine

HCID 783445-Bromopyrimidine

Product 1

HCID 21940661HCID 21940661, compoundYield 85%

Procedure

Using the general procedure, 5-bromopyrimidine (159 mg, 1.0 mmol) was coupled with 4-methoxybenzylamine (196 μL, 1.5 mmol) at 90° C. for 22 h. Purification of the crude product by column chromatography on silica gel using dichloromethane (saturated with ammonia)/ethyl acetate (1:1) as eluent afforded the desired product as a white solid (183 mg, 85% yield). Rf=0.2 (dichloromethane (saturated with ammonia)/ethyl acetate=1:1).

Workup

customPurification of the crude product by column chromatography on silica gel

Sources & evidence

ORD record: ord-66420ca1f7984cce999c81c8c7abd991
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06759554B2

Reaction notes

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