Cyclopentylamine → 2-(3-Chlorobenzyl)-4-(cyclopentylamino)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile

HRID 414964Notes

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.[CH:20]1([NH2:25])[CH2:24][CH2:23][CH2:22][CH2:21]1>>[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:25][CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[N:11]=1

Participants

Reactant 2

HCID 2906Cyclopentylamine

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

Product 1

HCID 1359951102-(3-Chlorobenzyl)-4-(cyclopentylamino)-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 292 mg (3.43 mmol) of cyclopentylamine to give 10 mg (9% of theory) of the title compound.

Sources & evidence

ORD record: ord-d55486cbbff1491a8299ee54761f3e57
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088769B2

Reaction notes

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