Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 3,4,5-Trimethoxyaniline | HCID 32285 | — |
| Reactant | HCID 68798028 | HCID 68798028 | — |
| Catalyst | Diethyl Ether | HCID 3283 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 68796093 | HCID 68796093 | 36.6% |
Reaction Steps
To a mixture of 4-{[2-(4-methylbenzoyl)phenyl]amino}-2-(methylsulfonyl) pyrimidine-5-carbonitrile (54 mg, 0.138 mmol) and 3,4,5-trimethoxyaniline (26 mg, 0.142 mmol) in absolute ethanol (3 ml) was added 1N HCl in diethyl ether (3 drops). The reaction was facilitated using microwave irradiation. The reaction was heated at 180° C. for 600 sec. using Personal Chemistry SmithSynthesizer. On cooling a crude yellow solid was collected by filtration. Pure sample was obtained after chromatography to give 4-{[2-(4-methylbenzoyl)phenyl]amino}-2-[(3,4,5-trimethoxyphenyl)amino]pyrimidine-5-carbonitrile (25 mg, %) as a canary yellow solid. 1H NMR (DMSO-d6): δ 10.0 (s, 1H), 9.39 (br s, 1H), 8.39 (s, 1H), 8.04 (d, 1H, J=8.4 Hz), 7.58-7.48 (m, 4H), 7.28 (t, 1H, J=7.6 Hz), 7.22 (d, 2H, J=7.9 Hz), 6.91 (s, 1H), 3.65 (s, 3H), 3.61 (s, 6H), 2.35 (s, 3H); ES-MS m/z 496 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07514446B2 |
|---|
| Source dataset | uspto-grants-2009_04 |
|---|
| ORD ID | ord-ae9568f560e841239eaa4f12ec2a3e43 |
|---|
| Source note | uspto-grants-2009_04 |
|---|