Diisobutylaluminumhydride → 4-Chloro-2-(4-hydroxybutyl)-6-morpholinopyrimidine

HRID 2375178Notes

Reaction equation

HRID 2375178 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([CH2:14][CH2:15][CH2:16][C:17](OCC)=[O:18])[N:3]=1.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([CH2:14][CH2:15][CH2:16][CH2:17][OH:18])[N:3]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 220469094-Chloro-2-(4-ethoxy-4-oxo-butyl)-6-morpholinopyrimidine

Product 1

HCID 220469294-Chloro-2-(4-hydroxybutyl)-6-morpholinopyrimidineYield 79.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-chloro-2-(4-ethoxy-4-oxo-butyl)-6-morpholinopyrimidine (1.108 g, 3.54 mmol) in 50 mL THF at −78° C., a diisobutylaluminum hydride (DIBAL) solution (4.72 mL 1.5 M in Toluene, 7.08 mmol) was slowly added. After addition, the obtained reaction mixture was warmed up slowly to 0° C. and kept at 0° C. for 10 min. After routine workup, flash chromatography was performed to obtain 4-chloro-2-(4-hydroxybutyl)-6-morpholinopyrimidine (0.76 g, 2.80 mmol, 79%) as light yellow solid.

Workup

  1. additionAfter addition
  2. customthe obtained reaction mixture

Sources & evidence

ORD record
ord-96b27f5a869e4707b4d251c1d3aa7726
Source dataset
uspto-grants-2008_12
Patent number
US07465725B2

Reaction notes

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