Hydrazine hydrate (1:1) → 5-(aminomethyl)-N-(3-chlorophenyl)-4-(trifluoromethyl)pyrimidin-2-amine

HRID 38772Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12]([CH2:19][N:20]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.O.NN>CO>[NH2:20][CH2:19][C:12]1[C:13]([C:15]([F:18])([F:17])[F:16])=[N:14][C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[N:10][CH:11]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To the crude 2-({2-[(3-chlorophenyl)amino]-4-(trifluoromethyl)pyrimidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione obtained in Preparative Example 13 were added methanol (15 mL) and hydrazine monohydrate (0.125 mL) at room temperature, followed by stirring at 60° C. for 4.5 hours. The resulting precipitate was removed by filtration and the filtrate was concentrated, and then, the obtained residue was purified by silica gel column chromatography (eluent: chloroform-methanol) to obtain 5-(aminomethyl)-N-(3-chlorophenyl)-4-(trifluoromethyl)pyrimidin-2-amine (105 mg) as a pale yellow powder.

Workup

customThe resulting precipitate was removed by filtration
concentrationthe filtrate was concentrated
customthe obtained residue was purified by silica gel column chromatography (eluent: chloroform-methanol)

Sources & evidence

ORD record: ord-58232f56be3d445e9bed62016106b978
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524727B2

Reaction notes

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