Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | 4-Aminoacetanilide | HCID 31230 | — |
| Reactant | HCID 21995278 | HCID 21995278 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Solvent | Acetonitrile--water (1/1) | HCID 18373917 | — |
| Product | HCID 10369553 | HCID 10369553 | 72% |
Reaction Steps
To a mixture of 5-bromo-2-chloro-N-(3,4,5-trimethoxyphenyl)pyrimidin-4-amine (67 mg, 0.178 mmol) and N-(4-aminophenyl)acetamide (28 mg, 0.185 mmol) in 2-propanol (2 mL) was added 1N HCl in diethyl ether (50 uL, 0.05 mmol). The reaction mixture was heated at 90° C. for approx. 36 hours. After the reaction was cooled to room temperature the mixture was taken up in 1:1 acetonitrile/H2O (60 mL) and lyopholized to give N-[4-({5-bromo-4-[(3,4,5-trimethoxyphenyl)amino]pyrimidin-2-yl}amino)phenyl]acetamide hydrochloride (67 mg, 72%) as a grey solid. 1H NMR (DMSO-d6/D2O): δ 8.21 (s, 1H), 7.25-7.67 (m, 4H), 6.87 (s, 2 H), 3.70 (s, 3 H), 3.69 (s, 6 H), 2.00 (s, 3H). MS m/z 488 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07514446B2 |
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| Source dataset | uspto-grants-2009_04 |
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| ORD ID | ord-b44ebf7607dc4ad182c47851c891868d |
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| Source note | uspto-grants-2009_04 |
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