Ammonia → 5-Chloro-2-cyclopropyl-6-(diethoxymethyl)-4-pyrimidinamine
Reaction equation
[NH3:1].Cl[C:3]1[C:8]([Cl:9])=[C:7]([CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[N:6]=[C:5]([CH:17]2[CH2:19][CH2:18]2)[N:4]=1>C(O)C>[Cl:9][C:8]1[C:3]([NH2:1])=[N:4][C:5]([CH:17]2[CH2:19][CH2:18]2)=[N:6][C:7]=1[CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
Ethanol (190 mL) was saturated with ammonia. 4,5-Dichloro-2-cyclopropyl-6-(diethoxymethyl)pyrimidine (i.e. the product of Example 5) (25.2 g, 86.5 mmol) was added, and the mixture sealed in a pressure vessel (Parr Instrument Co., Moline, Ill.). The mixture was warmed to 75° C., and the pressure was maintained at 40 psi (276 kPa). After 8 h at this temperature and pressure the mixture was allowed to cool to room temperature. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (200 mL) and then filtered. The filtrate was evaporated under reduced pressure, and the residue was taken up in hexanes to crystallize the product as an off-white solid (19.97 g, 85% yield). The product recrystallized from hexanes had a melting point of 104.5-109.5° C.
Workup
- customthe mixture sealed in a pressure vessel (Parr Instrument Co., Moline, Ill.)
- temperaturethe pressure was maintained at 40 psi (276 kPa)
- temperatureto cool to room temperature
- customThe solvent was removed under reduced pressure
- dissolutionThe residue was dissolved in ethyl acetate (200 mL)
- filtrationfiltered
- customThe filtrate was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-b5db39fbe024451a9f5dbd795760fd1c
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08013155B2
Reaction notes
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