Hydrazine hydrate (1:1) → {6-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidin-4-yl}-hydrazine
Reaction equation
Cl[C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][N:18]=2)[N:5]=[CH:4][N:3]=1.C(C1C(Cl)=NC=NC=1CBr)CC.FC1C(C2NC=CN=2)=NC=CC=1.O.[NH2:49][NH2:50]>CCO>[F:23][C:22]1[C:17]([C:13]2[N:12]([CH2:11][C:6]3[N:5]=[CH:4][N:3]=[C:2]([NH:49][NH2:50])[C:7]=3[CH2:8][CH2:9][CH3:10])[CH:16]=[CH:15][N:14]=2)=[N:18][CH:19]=[CH:20][CH:21]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 4-chloro-6-[2-(3-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidine (prepared from 5-propyl-6-bromomethyl-4-chloro-pyrimidine and 3-fluoro-2-(1H-imidazol-2-yl)-pyridine essentially as described in Example 1) (2.5 g, 7.5 mmol) and hydrazine monohydrate (1.37 g, 27.4 mmol) in EtOH (15 mL) is heated in a sealed tube at 70° C. overnight. The solvent is removed in vacuo and the residue is triturated with ethyl acetate and ethyl ether. Filtration gives a white solid (131) which is used in the next step without further purification.
Workup
- customThe solvent is removed in vacuo
- customthe residue is triturated with ethyl acetate and ethyl ether
- filtrationFiltration
Sources & evidence
- ORD record
- ord-6e3a17f9a35e4b42909332e337c702c5
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07271170B2
Reaction notes
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