Methylamine → 1-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-methylmethanamine

HRID 41892

Reaktionsgleichung

Reaktionsgleichung von HRID 41892
[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH:11]=O)=[CH:8][C:6]=2[N:7]=1.C1COCC1.[CH3:24][NH2:25]>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH2:11][NH:25][CH3:24])=[CH:8][C:6]=2[N:7]=1

Komponenten

6

Edukt 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Produkt 1

HCID 595929371-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-methylmethanamineAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

2-Chloro-4-morpholinothieno[3,2-c]pyrimidine-6-carbaldehyde 10 (2.0 g) was dissolved in 50 mL toluene and 50 mL THF followed by the addition of 20 mL of 40% methylamine in H2O. The reaction mixture was stirred at room temp under N2 for 24 hours. The solvents were removed in vacuo and the residue was dissolved in 50 mL methanol and 50 mL THF and the NaBH4 added portion-wise. This reaction mixture was stirred at room temp under N2 for 24 hours and complete reaction was confirmed by LCMS. The solvents were removed in vacuo and the crude product purified by flash chromatography (EtOAc/EtOH) to give 1.12 g 35 (53% yield). MS (Q1) 300 (M+).

Aufarbeitung

  1. customThe solvents were removed in vacuo
  2. dissolutionthe residue was dissolved in 50 mL methanol
  3. stirringThis reaction mixture was stirred at room temp under N2 for 24 hours
  4. customcomplete reaction
  5. customThe solvents were removed in vacuo
  6. customthe crude product purified by flash chromatography (EtOAc/EtOH)

Quellen und Nachweise

ORD-Eintrag
ord-fdcd8acac1394311b9988989ddd68e8f
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536161B2

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