Acetic Acid → Methyl 2-(3-((4-(2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)butylamino)methyl)phenyl)acetate

HRID 2387786Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2387786
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[C:7]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[N:8][C:9]([NH2:13])=[N:10][C:11]=1[CH3:12].[CH:20]([C:22]1[CH:23]=[C:24]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:25]=[CH:26][CH:27]=1)=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[NH2:13][C:9]1[N:10]=[C:11]([CH3:12])[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH:1][CH2:20][C:22]2[CH:23]=[C:24]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:25]=[CH:26][CH:27]=2)=[C:7]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[N:8]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 11819590Methyl 2-(3-formylphenyl)acetateHCID 684176515-(4-Aminobutyl)-6-methyl-N4-pentylpyrimidine-2,4-diamine

Produkt 1

HCID 42612993Methyl 2-(3-((4-(2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)butylamino)methyl)phenyl)acetateAusbeute 6,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To the product of step (ii) (0.06 g), methyl 2-(3-formylphenyl)acetate (0.0403 g) and acetic acid (0.0136 g) in THF (10 mL) was added sodium triacetoxyborohydride (0.1102 g). The reaction mixture was stirred for 72 h, the solvents were evaporated and the residue dissolved in MeOH, acidified and purified via SCX resin, then RPHPLC to give the title compound 6 mg.

Aufarbeitung

  1. customthe solvents were evaporated
  2. dissolutionthe residue dissolved in MeOH
  3. custompurified via SCX resin

Quellen und Nachweise

ORD-Eintrag
ord-cfb2313995c9489992d95ee3d95d3961
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268990B2

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