Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Bicarbonate Ion | HCID 769 | — |
| Reactant | N-Methyl-1,3-propanediamine | HCID 80511 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (2-Chloroquinazolin-4-yl)-(4-methoxyphenyl)-methylamine hydrochloride | HCID 86639964 | — |
| Solvent | 1-Butanol | HCID 263 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | Ammonium Hydroxide | HCID 14923 | — |
| Product | N2-(3-Amino-propyl)-N4-(4-methoxy-phenyl)-N2,N4-dimethyl-quinazoline-2,4-diamine | HCID 59242013 | — |
Reaction Steps
A mixture of (2-chloro-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine hydrochloride (203 mg, 0.604 mmol), ethyl-diisopropyl-amine (0.25 mL, 1.4 mmol) and N1-methyl-propane-1,3-diamine (95%; 100 μL) in n-butanol (4 mL) was heated at 115° C. After 32 h, the rxn was treated with bicarbonate resin (Novabiochem 01-64-0419) then concd. The material was dissolved in CHCl3, adsorbed onto diatomaceous earth and partially purified on an amine column (Isco 68-2203-101) eluting with a gradient of 0-100% i-PrOH in CHCl3. Pure title compound was obtained as a pale yellow oil (23 mg; 11%) after preparative TLC (SiO2/100:20:2 CHCl3:MeOH:concd NH4OH). 1H NMR (DMSO-d6) δ 7.38-7.27 (m, 2H), 7.16 (m, 2H), 6.97 (m, 2H), 6.79 (d, J=8.4 Hz, 1H), 6.65 (m, 1H), 3.77 (s, 3H), 3.76 (m, 2H), 3.44 (s, 3H), 3.17 (s, 3H), 2.63 (t, J=6.6 Hz, 2H), 1.75 (m, 2H); LC-MS (ESI+; 352 ([M+H]+)).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08309562B2 |
|---|
| Source dataset | uspto-grants-2012_11 |
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| ORD ID | ord-d714858c2f994b239f5d0542fb54612f |
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| Source note | uspto-grants-2012_11 |
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