Methylamine → 6-[(Methylamino)methyl]-2-(trifluoromethyl)pyrimidine-4-carboxylic acid

HRID 1617404Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1617404
[CH3:1][NH2:2].Br[CH2:4][C:5]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:8]=[C:7]([C:15]([O:17]CC)=[O:16])[CH:6]=1.O.[OH-].[Li+]>C(Cl)Cl.O>[CH3:1][NH:2][CH2:4][C:5]1[N:10]=[C:9]([C:11]([F:12])([F:13])[F:14])[N:8]=[C:7]([C:15]([OH:17])=[O:16])[CH:6]=1

Komponenten

6

Edukt 3

HCID 6329MethylamineHCID 168937Lithium hydroxide, monohydrateHCID 58431340Ethyl 6-(bromomethyl)-2-(trifluoromethyl)pyrimidine-4-carboxylate

Produkt 1

HCID 673911066-[(Methylamino)methyl]-2-(trifluoromethyl)pyrimidine-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of methylamine (33 wt % in Ethanol, 1.12 mmol, Aldrich) was added portionwise to a solution of ethyl 6-(bromomethyl)-2-(trifluoromethyl)pyrimidine-4-carboxylate (0.150 g, 0.321 mmol, Example 5, Step A) in methylene chloride (3.0 mL), until reaction was complete. Solvent was removed in vacuo. The residue was dissolved in tetrahydrofuran (7.0 mL) and water (2.0 mL), and lithium hydroxide monohydrate (0.135 g, 3.21 mmol) was added. After a 5 minute reaction time, the mixture was treated with 1N HCl to adjust the pH to 7, then was purified using preparative HPLC-MS (C18 eluting with a gradient of MeCN/H2O containing 0.15% NH4OH). LC-MS: 236.1 (M+H)+.

Aufarbeitung

  1. customSolvent was removed in vacuo
  2. dissolutionThe residue was dissolved in tetrahydrofuran (7.0 mL)
  3. customAfter a 5 minute reaction time
  4. customwas purified
  5. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-79291a06aef941f1ac41ce5f4f16b700
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765734B2

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