Hydrazine hydrate (1:1) → 2-(2,6-Dimethyl-4-(pyrimidin-5-yl)phenoxy)acetohydrazide

HRID 63367Notes

Reaction equation

N[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:19]=[C:18]([CH3:20])[C:11]([O:12][CH2:13][C:14]([NH:16][NH2:17])=[O:15])=[C:10]([CH3:21])[CH:9]=2)=[CH:4][N:3]=1.NC1N=CC(C2C=C(C)C(OCC(OC)=O)=C(C)C=2)=CN=1.O.NN>CCO>[CH3:20][C:18]1[CH:19]=[C:8]([C:5]2[CH:6]=[N:7][CH:2]=[N:3][CH:4]=2)[CH:9]=[C:10]([CH3:21])[C:11]=1[O:12][CH2:13][C:14]([NH:16][NH2:17])=[O:15]

Participants

Conditions

Temperature: 100 °C

Procedure

Synthesis of 2-(4-(2-aminopyrimidin-5-yl)-2,6-dimethylphenoxy)acetohydrazide: methyl 2-(4-(2-aminopyrimidin-5-yl)-2,6-dimethylphenoxy)acetate (0.28 g, 1 mmol) was dissolved in EtOH. Hydrazine monohydrate (0.06 g, 1.2 mmol) was added thereto, followed by stirring at 100° C. for 8 hours under reflux. After the completion of the reaction, the reaction mixture was concentrated under reduced pressure. The formed solid was filtered to obtained 2-(2,6-dimethyl-4-(pyrimidin-5-yl)phenoxy)acetohydrazide (0.31 g, 100%).

Workup

temperatureunder reflux
customAfter the completion of the reaction
concentrationthe reaction mixture was concentrated under reduced pressure
filtrationThe formed solid was filtered

Sources & evidence

ORD record: ord-68ed788905d4488b95b05c8e4cd30e60
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447083B2

Reaction notes

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