Ethanol → HCID 117821247, compound

HRID 59063Notes

Reaction equation

HRID 59063 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[C:5]([CH3:10])=[C:4]([Cl:11])[N:3]=1.C(O)C>C(O)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[C:5]([CH3:10])=[C:4]([Cl:11])[N:3]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 117821434HCID 117821434, compound

Product 1

HCID 117821247HCID 117821247, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

To a solution of 2,6-dichloro-5-methylpyrimidine-4-carbaldehyde (0.325 g, 1.70 mmol) in ethanol (10 mL) sodium borohydride (0.032 g, 0.85 mmol) was added at 0° C. The mixture was stirred for 10 minutes. Acetic acid (4 drops) was added and the volatiles were removed in vacuum. The residue was treated with 10% solution of methanol in chloroform (10 mL). The slurry was filtered through a pad of silica gel. The filtrate was concentrated and purified by column chromatography on silica using a gradient 0-4% of methanol in dichloromethane as eluent to yield the title product, 0.23 g (71%).

Workup

  1. customthe volatiles were removed in vacuum
  2. additionThe residue was treated with 10% solution of methanol in chloroform (10 mL)
  3. filtrationThe slurry was filtered through a pad of silica gel
  4. concentrationThe filtrate was concentrated
  5. custompurified by column chromatography on silica using a gradient 0-4% of methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-5160cdc127074f6cbfd36d4a3f8464b3
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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