2-Methoxyethylamine → 2-(3-Chlorobenzyl)-4-[(2-methoxyethyl)amino]-6-oxo-1,6-dihydropyrimidine-5-carbonitrile

HRID 414967Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][C:6]1[NH:7][C:8](=[O:16])[C:9]([C:14]#[N:15])=[C:10](SC)[N:11]=1.[CH3:20][O:21][CH2:22][CH2:23][NH2:24]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][C:6]1[NH:7][C:8](=[O:16])[C:9]([C:14]#[N:15])=[C:10]([NH:24][CH2:23][CH2:22][O:21][CH3:20])[N:11]=1

Participants

Reactant 2

HCID 80182-Methoxyethylamine

HCID 584078022-(3-Chlorobenzyl)-4-(methylsulphanyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile

Product 1

HCID 1359951262-(3-Chlorobenzyl)-4-[(2-methoxyethyl)amino]-6-oxo-1,6-dihydropyrimidine-5-carbonitrile

Procedure

In analogy to the preparation of Example 1, 100 mg (0.34 mmol) of 2-(3-chlorobenzyl)-4-(methylsulphanyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile are reacted with 257 mg (3.43 mmol) of 2-methoxyethylamine to give 61 mg (56% of theory) of the title compound.

Sources & evidence

ORD record: ord-6f1c8c7822014db5a8d99688561bc42a
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088769B2

Reaction notes

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