Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-chloro-6-isopropylpyrimidin-2-amine | HCID 2773619 | — |
| Reactant | HCID 67198236 | HCID 67198236 | — |
| Product | HCID 67200057 | HCID 67200057 | 30% |
Reaction Steps
A mixture of Intermediate 6 (100 mg, 0.32 mmol), 2-amino-4-chloro-6-isopropylpyrimidine (58 mg, 0.38 mmol) and sodium hydride (60% in mineral oil, 18 mg, 0.45 mmol) in DMF (2 mL) was stirred at 100° C. for 45 minutes. Purification was by preparative HPLC (Method 1) followed by partitioning between DCM (20 mL) and 10% aqueous K2CO3 solution (10 mL). The organic layer was separated, dried (MgSO4) and concentrated in vacuo to give the title compound as a white solid (37 mg, 30%). δH (CDCl3) 8.32 (s, 1H), 7.71-7.77 (m, 2H), 7.69 (d, J 8.1 Hz, 1H), 7.57 (d, J 9 Hz, 1H), 7.41-7.53 (m, 4H), 6.03 (s, 1H), 5.47 (s, 2H), 4.82 (br s, 2H), 2.83 (s, 3H), 2.64-2.79 (m, 1H), 1.21 (d, J 7 Hz, 6H). LCMS (ES+) 385.2 (M+H)+, RT 2.92 minutes (Method 3).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08399483B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-4cbb12c402af45b1b0abb02581bf53e1 |
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| Source note | uspto-grants-2013_03 |
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