Sodium borohydride → 5-(3,4,5,6,7,8-hexahydro-1H-isoquinolin-2-ylmethyl)-2-methyl-pyrimidin-4-ylamine

HRID 2294015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2294015
Cl.[Cl-].[NH2:3][C:4]1[C:9]([CH2:10][N+:11]2[CH:20]=[CH:19][C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[CH:12]=2)=[CH:8][N:7]=[C:6]([CH3:21])[N:5]=1.[BH4-].[Na+]>CO>[CH2:12]1[C:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:18]=2[CH2:19][CH2:20][N:11]1[CH2:10][C:9]1[C:4]([NH2:3])=[N:5][C:6]([CH3:21])=[N:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 214736402-(4-Amino-2-methyl-pyrimidin-5-ylmethyl)-5,6,7,8-tetrahydro-isoquinolinium chloride hydrochloride

Produkt 1

HCID 214736565-(3,4,5,6,7,8-hexahydro-1H-isoquinolin-2-ylmethyl)-2-methyl-pyrimidin-4-ylamineAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 9.81 g (0.030 mol) of 2-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5,6,7,8-tetrahydro-isoquinolinium chloride hydrochloride in 50 ml of methanol was treated portionwise at 10° with 3.5 g (0.092 mol) of sodium borohydride. The mixture was stirred at room temperature for 1 hour and completely freed from the solvents. The residue was partitioned between ethyl acetate and water, extracted and recrystallized from petroleum ether. 5.7 g (74%) of 5-(3,4,5,6,7,8-hexahydro-1H-isoquinolin-2-ylmethyl)-2-methyl-pyrimidin-4-ylamine were obtained as white crystals; m.p. 137°-139° (dec.).

Aufarbeitung

  1. customThe residue was partitioned between ethyl acetate and water
  2. extractionextracted
  3. customrecrystallized from petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-00dbf01a775143f1adb126efcac2b380
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05688798

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