Hydrazine → 2,5-Dimethoxy-4-hydrazinopyrimidine
Reaction equation
Cl[C:2]1[C:7]([O:8][CH3:9])=[CH:6][N:5]=[C:4]([O:10][CH3:11])[N:3]=1.[NH2:12][NH2:13]>CO>[CH3:11][O:10][C:4]1[N:3]=[C:2]([NH:12][NH2:13])[C:7]([O:8][CH3:9])=[CH:6][N:5]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A slurry of 4-chloro-2,5-dimethoxypyrimidine (3.0 grams (g), 17.2 mmol) in methanol (15 milliliters (mL)) was treated with aqueous hydrazine (3.9 g of 35 wt. %, 42.5 mmol) in one portion causing a slow exotherm to 29° C. The reaction was then warmed to 50° C. and held at that temperature for 2 hours (h) at which time gas chromatography (GC) analysis indicated the reaction was complete. The clear solution was cooled to ambient temperature and allowed to stir overnight. The solvent was removed in vacuo and the resulting gummy solid was triturated with CH3CN (50 mL). The resulting mixture was filtered through a pad of silica gel (6 centimeter (cm)×6 cm). The pad was rinsed with CH3CN (550 mL). The filtrates were combined and the solvent removed in vacuo affording the title compound as a white solid (2.6 g, 89%): mp 115-117° C.; 1H NMR (300 MHz, DMSO-d6) 3.73 (s, 3H), 3.76 (s, 3H), 4.29 (bs, 2H), 7.51 (s, 1H), 8.23 (bs, 1H); MS(GC, 70eV) 170 (M+, 100%), 155(55%), 151 (40%).
Workup
- customto 29° C
- temperatureThe clear solution was cooled to ambient temperature
- customThe solvent was removed in vacuo
- customthe resulting gummy solid was triturated with CH3CN (50 mL)
- filtrationThe resulting mixture was filtered through a pad of silica gel (6 centimeter (cm)×6 cm)
- washThe pad was rinsed with CH3CN (550 mL)
- customthe solvent removed in vacuo
Sources & evidence
- ORD record
- ord-21aca26eb0644f4db1d5ee014ad882e5
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06362335B1
Reaction notes
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