Potassium Carbonate → 2-(1-(6-hydrazinyl-2-methylpyrimidin-4-yl)azetidin-3-yl)-1-methyl-1H-benzo[d]imidazole

HRID 1486756Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[CH2:12][CH:11]([C:13]3[N:17]([CH3:18])[C:16]4[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=4[N:14]=3)[CH2:10]2)[CH:3]=1.O.[NH2:24][NH2:25].C([O-])([O-])=O.[K+].[K+]>CC1OCCC1>[NH:24]([C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[CH2:12][CH:11]([C:13]3[N:17]([CH3:18])[C:16]4[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=4[N:14]=3)[CH2:10]2)[CH:3]=1)[NH2:25]

Participants

Conditions

Temperature: 85 °C

Procedure

Compound 2-2 (900 mg, 2.87 mmol), hydrazine hydrate (431 mg, 8.6 mmol) and K2CO3 (1.2 g, 8.6 mmol) were suspended in 2-MeTHF (8 mL) in a vial that was capped and heated at 85° C. for 16 h. After cooling to room temperature, the reaction was filtered and the collected solids were washed with water and ether and dried over suction to give Intermediate 2 as a white solid. MS: m/z=310.3 (M+H).

Workup

customthat was capped
temperatureAfter cooling to room temperature
filtrationthe reaction was filtered
washthe collected solids were washed with water and ether
customdried over suction

Sources & evidence

ORD record: ord-99a7b5a907284146b51df57cbac5a33f
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428492B2

Reaction notes

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