Sodium borohydride → 8-[(4-Bromophenyl)methyl]4-hydroxymethyl-2-methyl-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one

HRID 129013Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 129013
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:14]3[N:15]=[C:16]([CH3:21])[N:17]=[C:18]([CH:19]=[O:20])[C:13]=3[CH2:12][CH2:11][C:10]2=[O:22])=[CH:4][CH:3]=1.[BH4-].[Na+]>O1CCCC1.C(O)(C)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:14]3[N:15]=[C:16]([CH3:21])[N:17]=[C:18]([CH2:19][OH:20])[C:13]=3[CH2:12][CH2:11][C:10]2=[O:22])=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 104285708-[(4-Bromophenyl)methyl]-2-methyl-7-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-4-carbaldehyde

Produkt 1

HCID 104737918-[(4-Bromophenyl)methyl]4-hydroxymethyl-2-methyl-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-oneAusbeute 122,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 8-[(4-bromophenyl)methyl]-2-methyl-7-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-4-carbaldehyde (550 mg, 1.53 mmol) in tetrahydrofuran (5 mL) and isopropanol (2 mL) was added sodium borohydride (116 mg, 3.05 mmol). After 45 min, the mixture was cooled to 0° C. and CO2 was bubbled in for 5 min. The mixture was filtered and the filtrate was concentrated to give 677 mg of a yellow foam. Purification by flash chromatography (5% MeOH/CH2Cl2) gave 496 mg (90%) of product as an off-white solid, mp 159°-160° C.

Aufarbeitung

  1. customCO2 was bubbled in for 5 min
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-d966a65b3dd74adca12b2024bdd8b2b5
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466692

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