Acetic Acid → (+)-9-{6-[(4-Methoxy-benzyl)-methyl-amino]-pyridin-2-yl}-3-pyrimidin-5-yl-non-4-enoic acid ethyl ester

HRID 2120670

Reaktionsgleichung

Reaktionsgleichung von HRID 2120670
[CH2:1]([O:3][C:4](=[O:35])[CH2:5][CH:6]([C:29]1[CH:30]=[N:31][CH:32]=[N:33][CH:34]=1)[CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[N:14]=1)[CH3:2].C=O.[C:38](O)(=O)C.[BH3-]C#N.[Na+]>CO>[CH2:1]([O:3][C:4](=[O:35])[CH2:5][CH:6]([C:29]1[CH:30]=[N:31][CH:32]=[N:33][CH:34]=1)[CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N:19]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH3:38])[N:14]=1)[CH3:2]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 69666458(+)9-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-3-pyrimidin-5-yl-non-4-enoic acid ethyl ester

Produkt 1

HCID 69665963(+)-9-{6-[(4-Methoxy-benzyl)-methyl-amino]-pyridin-2-yl}-3-pyrimidin-5-yl-non-4-enoic acid ethyl esterAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 6-10 (1.6 g, 3.37 mmol) in methanol (30 mL) was added paraformaldehyde (0.80 g) and acetic acid (0.96 mL, 16.8 mmol). After stirring at 50° C. for 15 minutes, NaCNBH3 (0.275 g, 4.38 mmol) was added and the mixture stirred for an additional 30 minutes at 50° C. Evaporation of the solvents and purification on silica gel (5% MeOH/CHCl3) afforded 6-10 in 75% yield.

Aufarbeitung

  1. stirringthe mixture stirred for an additional 30 minutes at 50° C
  2. customEvaporation of the solvents and purification on silica gel (5% MeOH/CHCl3)
  3. customafforded 6-10 in 75% yield

Quellen und Nachweise

ORD-Eintrag
ord-3778aafc098a413aab222afa943d3a9a
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06693101B2

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