Tetrahydrofuran → HCID 178432754, compound

HRID 1501104Notes

Reaction equation

HRID 1501104 reaction equation
[OH:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[N:5]=[C:4]([CH3:11])[N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1>O>[NH2:9][CH2:8][C:7]1[C:2]([OH:1])=[N:3][C:4]([CH3:11])=[N:5][C:6]=1[CH3:10]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 1784327532,6-dimethyl-4-oxo-1H-pyrimidine-5-carbonitrile

Product 1

HCID 178432754HCID 178432754, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-hydroxy-2,6-dimethylpyrimidine-5-carbonitrile (2.7 g, 18.1 mmol), lithium aluminium hydride (2.1 g, 54.3 mmol), and tetrahydrofuran (80 mL) was stirred at 25° C. for 4 hours. Water (5 mL) was added to the mixture. The mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1) to give 5-(aminomethyl)-2,6-dimethylpyrimidin-4-ol as a white solid (525 mg, 19%). LRMS (M+H+) m/z: calcd 153.09. found 153.

Workup

  1. concentrationThe mixture was concentrated
  2. customto give a residue
  3. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1)

Sources & evidence

ORD record
ord-c7968c26707b45c68a7b67f36b2afc8b
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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