HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → 4-Amino-6-{[1-(3-bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethyl]amino}pyrimidine-5-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-Amino-6-chloropyrimidine-5-carbonitrile | HCID 12278262 | — |
| Reactant | 1-(3-Bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethanamine | HCID 86666916 | — |
| Product | 4-Amino-6-{[1-(3-bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethyl]amino}pyrimidine-5-carbonitrile | HCID 86711469 | 54% |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
A mixture of 1-(3-bromo-5-chloro-4-fluoro-2-methoxyphenyl)ethanamine (40 mg, 0.14 mmol), 4-amino-6-chloropyrimidine-5-carbonitrile (J & W PharmLab, #70-0156 33 mg, 0.21 mmol) and N,N-diisopropylethylamine (74 μL, 0.43 mmol) in ethanol (1.6 mL, 27 mmol) was heated at 100° C. overnight. Purification by preparative LC/MS (pH10) gave the desired compound (54% yield). LCMS calculated for C14H13BrClFN5O (M+H)+: m/z=400.0, 402.0. found: 400.0, 402.0. 1H NMR (300 MHz, DMSO-d6): δ 7.95 (s, 1H), 7.77 (m, 1H), 7.28 (br s, 2H), 5.56 (m, 1H), 3.92 (s, 1H), 1.40 (m, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09126948B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-22d9501d5b304e4baa3ea742a925fb54 |
| Source note | uspto-grants-2015_09 |