Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2,4-Dichloro-6-morpholino-1,3,5-triazine | HCID 81076 | — |
| Reactant | tert-Butyl 3-(aminomethyl)azetidine-1-carboxylate--hydrogen chloride (1/1) | HCID 45072199 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86636517 | HCID 86636517 | 46% |
Reaction Steps
To a solution of the 3-aminomethyl-azetidine-1-carboxylic acid tert-butyl ester HCl salt (945 mg, 4.24 mmol) and NEt3 (856 mg, 8.48 mmol) in THF (10 mL) at 0° C. was added a suspension of 2,4-dichloro-6-morpholin-4-yl-[1,3,5]triazine (996 mg, 4.24 mmol) at 0° C. The reaction mixture was stirred for another 1 hr at 0° C. and allowed to warm to 20° C. and stirred for 1-4 hrs to drive the reaction to completion. Silica gel (20 g) was added to the reaction mixture and the solvent was removed so that product was adsorbed on the silica gel. The silica gel plug was placed on top of a column to purify by flash chromatography using CH2Cl2/MeOH/NH3 (20:1:01) eluent. After unifying the product fraction, and evaporation of solvent, (750 mg, 46% yield) product was obtained as yellow solid; MS (ESI) m/z 385
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08445486B2 |
|---|
| Source dataset | uspto-grants-2013_05 |
|---|
| ORD ID | ord-63f292f76e3e4e2abaa3c353c1b65940 |
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| Source note | uspto-grants-2013_05 |
|---|
