Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Piperazine | HCID 4837 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 136400722 | HCID 136400722 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 69057717 | HCID 69057717 | 91.6% |
Reaction Steps
A solution of 4-amino-2-chloro-2-methylpyrimidine-5-carbonitrile (Maybridge, 100 mg, 0.6 mmol), piperazine (207 mg, 2.4 mmol), and triethylamine (71 mg, 0.7 mmol) in N,N-dimethylacetamide (20 ml) was heated to 108° C. for 6 h. The reaction mixture was stirred at ambient temperature for 18 h before pouring into water (400 ml) and extracting with ethyl acetate (3×30 ml), and then dichloromethane (20 ml). The combined organic extracts were washed with water (3×150 ml), and then dried (MgSO4) and concentrated to give a yellow solid (120 mg). The crude solid was pre-absorbed onto silica gel (250 mg) and then purified by flash chromatography on silica gel (20 g) eluting with ethyl acetate:methanol (90:10 and then 80:20) to give the title compound as a white solid (28 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07494992B2 |
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| Source dataset | uspto-grants-2009_02 |
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| ORD ID | ord-c9a7bb872c0f445dbca874b4ddf84c9d |
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| Source note | uspto-grants-2009_02 |
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