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Hydrazine → 5-Fluoro-4-hydrazino-2-methyl-6-(1-pyrrolidinyl)pyrimidine

HRID 1366386
Notes
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Reaction equation

HRID 1366386 reaction equation
Cl[C:2]1[C:7]([F:8])=[C:6](Cl)[N:5]=[C:4]([CH3:10])[N:3]=1.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.CCN(C(C)C)C(C)C.[NH2:25][NH2:26]>CS(C)=O>[F:8][C:7]1[C:2]([NH:25][NH2:26])=[N:3][C:4]([CH3:10])=[N:5][C:6]=1[N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 9321HydrazineHCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 137310334,6-Dichloro-5-fluoro-2-methylpyrimidine

Product 1

HCID 669360205-Fluoro-4-hydrazino-2-methyl-6-(1-pyrrolidinyl)pyrimidineYield 59%

Reagents, catalysts & solvents 1

HCID 679
Dimethyl Sulfoxide
Solvent

Procedure

4,6-Dichloro-5-fluoro-2-methylpyrimidine (100 mg, 0.55 mmol) was dissolved in 2 mL of DMSO and stirred at room temperature. Pyrrolidine (50 μL, 0.61 mmol) was added, followed by DIPEA (210 μL, 1.21 mmol). The resulting reaction mixture was stirred for 2 h, and then hydrazine was added (1.0 mL) and the contents were heated to 80° C. for 1 h. The reaction mixture was then cooled to room temperature and purified by RP-HPLC to provide 5-fluoro-4-hydrazino-2-methyl-6-(1-pyrrolidinyl)pyrimidine (69 mg, 59%).

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 2 h
  3. temperaturethe contents were heated to 80° C. for 1 h
  4. temperatureThe reaction mixture was then cooled to room temperature
  5. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-01fd74a48af644eb9ae628a4a892ff0b
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07893056B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes