Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 135985849 | HCID 135985849 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 49869139 | HCID 49869139 | 55% |
Reaction Steps
To a 0° C. solution of 8-(1H-benzo[d]imidazol-2-yl)-3-methylimidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-one (0.54 mmol, 0.144 grams, 1 eq.) in anhydrous DMF (2.5 mL) was added sodium hydride 60% in mineral oil (0.59 mmol, 24 mg, 1.1 eq.) portion-wise. The formed suspension was stirred at low temperature for 10 minutes and methyl iodide (1.07 mmol, 67 μL, 2 eq.) was added into it in one portion. The suspension was stirred over night at room temperature. The reaction mixture was filtered and the obtained solid was washed with water, acetonitrile and ethyl acetate, and dried under vacuum to give the title compound. Yield: 55%. δH (DMSO-d6) 9.02 (1H, s), 7.77 (1H, d, J: 8.09), 7.68 (1H, d, J: 8.12), 7.36 (1H, m), 7.32 (1H, m), 4.14 (3H, s), 3.90 (3H, s).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09024018B2 |
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| Source dataset | uspto-grants-2015_05 |
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| ORD ID | ord-7f57a4aeee354360a25cbb7dc8c23e67 |
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| Source note | uspto-grants-2015_05 |
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