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

HRID 1486756
Notes
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Reaction equation

HRID 1486756 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 894935592-(1-(6-chloro-2-methylpyrimidin-4-yl)azetidin-3-yl)-1-methyl-1H-benzo[d]imidazole

Product 1

HCID 894937102-(1-(6-hydrazinyl-2-methylpyrimidin-4-yl)azetidin-3-yl)-1-methyl-1H-benzo[d]imidazole

Reagents, catalysts & solvents 1

HCID 73012-Methyltetrahydrofuran
Solvent

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

  1. customthat was capped
  2. temperatureAfter cooling to room temperature
  3. filtrationthe reaction was filtered
  4. washthe collected solids were washed with water and ether
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes