Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 4-Nitrophenethylamine | HCID 95153 | — |
| Reactant | HCID 57636101 | HCID 57636101 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 69065690 | HCID 69065690 | 59% |
Reaction Steps
By proceeding in a similar manner to Example 43(b) but substituting 2-(5-methoxy-1H-indol-3-yl)-ethylamine for 2-(4-nitro-phenyl)-ethylamine, and substituting acetonitrile for EtOH as solvent in Step 3 there is prepared [2-(5-methoxy-1H-indol-3-yl)-ethyl]-[2-methoxy-6-(3-methoxy-phenyl)-pyrimidin-4-yl]-amine which is dissolved in ether and treated with 1 M hydrogen chloride in ether affording [2-(5-methoxy-1H-indol-3-yl)-ethyl]-[2-methoxy-6-(3-methoxy-phenyl)-pyrimidin-4-yl]-amine hydrochloride [52.1 mg, 59%, Example 43(h)] as a solid. LC/MS: RT=2.45 minutes, MS: 405 (M+H). 1H NMR [300 MHz, (CD3)2SO]: □10.65 (1H, s), 7.41 (1H, m), 7.36 (2H, m), 7.2 (1H, m), 7.13 (2H, m), 7.01 (1H, m), 6.7 (1H, dd, J=9.6, 1.2 Hz), 6.6 (1H, s), 3.98 (3H, s), 3.8 (3H, s), 3.72 (3H, s), 3.56 (2H, m), 2.97 (2H, m).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07517889B2 |
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| Source dataset | uspto-grants-2009_04 |
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| ORD ID | ord-e607b9d797b647b9ae7305aae59b2b62 |
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| Source note | uspto-grants-2009_04 |
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